CAS: 945950-37-8; 4-Methyl-7H-Pyrrolo[2,3-D]Pyrimidine

该化合物是一种异环化合物,其特点是一个有引信的火花-芯核心,在4级有甲基替代成分.这一结构是医药化学的多种中间体,特别是在核糖浆模拟物和动脉抑制剂合成中.其硬性双环框架增强了与生物目标的结合性,而甲基组则可以影响再活性和溶性.该化合物因其在开发制药剂,包括潜在的抗癌和抗病毒治疗剂方面的作用而备受重视.高纯度可用于确保研究和工业应用的一致性.在标准条件下,其稳定性适合于多种合成变异.

英文名称4-Methyl-7H-Pyrrolo[2,3-D]Pyrimidine
中文名称4-甲基-7H-吡咯并[2,3-d]嘧啶
IUPAC名称4-methyl-7H-pyrrolo[2,3-d]pyrimidine
其它别名4-Methyl-7H-Pyrrolo[2,3-D]Pyrimidine; 4-Methyl-7H-Pyrrazolo[2,3-D]Pyrimidine; 7H-Pyrrolo[2,3-D]Pyrimidine, 4-Methyl-; 4-Methyl-1H-Pyrrolo[2,3-D]Pyrimidine
CAS编号945950-37-8
MFCD编号:MFCD13619883
EINECS号:895-723-9
FDA UNII编号:RZ4A845PGQ
分子式:C7H7N3
分子量:133.15
产品CID: 1997552
产品分类有机原料→分子砌块→芳杂环类化合物→吡咯类化合物

相似结构搜索
InChIKey: QWIAHMVNMONKCU-UHFFFAOYSA-N
InChI=1S/C7H7N3/c1-5-6-2-3-8-7(6)10-4-9-5/h2-4H,1H3,(H,8,9,10)…
计算化学: 氢键受体数2.0氢键供体数1.0可旋转键数0.0

相似化合物

1989623-62-2 119707-35-6 28266-84-2

MSDS等安全信息

GHS象形图
GHS符号GHS07;
注释: Exclamation mark
危险类别急性毒性类别4(经口)
警示词Warning(警告)
危险描述H302 |吞咽有害.
防范说明P261-P280-P302+P352

欧盟法规

REACH注册

上下游产品

7H-吡咯并[2,3-D]嘧啶 7H-Pyrrolo[2,3-D]Pyrimidine 271-70-5
2-甲基-7H-吡咯并[2,3-D]嘧啶(7Ci) 2-Methyl-7H-Pyrrolo[2,3-D]Pyrimidine 89792-07-4

合成工艺路线路线简述

合成目标产物 4-Methyl-7H-Pyrrolo[2,3-D]Pyrimidine 主要起始原料 Dimethylzinc And 4-Chloro-7H-Pyrrolo[2,3-D]Pyrimidine
3680-69-1 = 945950-37-8
反应条件:1.1 Reagents: Sodium Hydride Solvents: Tetrahydrofuran; 30 Min,0 - 15 °C1.2 Reagents: Tert-Butyldimethylsilyl Chloride Solvents: Tetrahydrofuran; 1 - 2 H,0 - 15 °C; 15 °C -> -10 °C1.3 Catalysts: Iron(Iii) Acetylacetonate Solvents: Tetrahydrofuran; -10 °C; < 15 °C; 2 H,15 - 30 °C1.4 Reagents: Ammonium Chloride Solvents: Water; < 10 °C1.5 Reagents: Ammonium Hydroxide Solvents: Water; 16 H,15 - 40 °C
标题:Industrial Process Synthesis Of Ruxolitinib Intermediate Salts Toward Jak Inhibitors
参考文献:World Intellectual Property Organization]

271-70-5 = 945950-37-8
反应条件:1.1 Reagents: Potassium Carbonate Catalysts: 2731734-19-1 Solvents: Toluene; 200 Min,Rt
标题:Preparation Of 7-Deazapurine Compounds Using Iron Complex Catalyst
参考文献:China]

2697704-48-4 = 945950-37-8
反应条件:1.1 Reagents: Potassium Hydroxide Solvents: Methanol; 1 H,Rt1.2 Reagents: Hydrochloric Acid Solvents: Water; Ph 6 - 7
标题:Preparation Method Of Key Intermediate Of Jak Inhibitor From 4-Chloro-7H-Pyrrolo[2,3-D]Pyrimidine For Treating Primarymyelofibrosis
参考文献:China]

3680-69-1 = 945950-37-8
反应条件:1.1 Catalysts: Iron Chloride (Fecl3) Solvents: Tetrahydrofuran,N-Methyl-2-Pyrrolidone; Rt -> 0 °C1.2 Solvents: Tetrahydrofuran; 2 H,0 °C -> Rt1.3 Reagents: Ammonium Chloride Solvents: Water; Rt
标题:Iron/copper Co-Catalyzed Cross-Coupling Reaction For The Synthesis Of 6-Substituted 7-Deazapurines And The Corresponding Nucleosides
作者:Li,Qingfeng; Persoons,Leentje; Daelemans,Dirk; Herdewijn,Piet
参考文献:Journal Of Organic Chemistry 日期:2020 卷标:85(2) 页码:403-418]

3680-69-1 = 945950-37-8
反应条件:1.1 Solvents: Tetrahydrofuran; 8 H,75 °C
标题:Structure Based Medicinal Chemistry Approach To Develop 4-Methyl-7-Deazaadenine Carbocyclic Nucleosides As Anti-Hcv Agent
作者:Thiyagarajan,Anandarajan; Salim,Mohammed T. A.; Balaraju,Tuniki; Bal,Chandralata; Baba,Masanori; Et Al
参考文献:Bioorganic & Medicinal Chemistry Letters 日期:2012 卷标:22(24) 页码:7742-7747]

3680-69-1 + 676-58-4 = 945950-37-8
反应条件:1.1 Catalysts: Iron(Iii) Acetylacetonate Solvents: Tetrahydrofuran; Rt; 8 H,Rt
标题:Preparation Of Purine Nucleoside Derivatives As Antitumor Agents And Inhibitors Of E1 Activating Enzymes
参考文献:World Intellectual Property Organization]

3680-69-1 = 945950-37-8
反应条件:1.1 Catalysts: Tetrakis(Triphenylphosphine)Palladium Solvents: Toluene,Tetrahydrofuran; 16 H,Rt -> 60 °C; 24 H,60 °C -> 80 °C; 80 °C -> 0 °C1.2 Reagents: Sodium Bicarbonate Solvents: Water; 0 °C
标题:Preparation Of Substituted Nucleoside Derivatives Useful As Anticancer Agents
参考文献:United States]

1989623-62-2 = 945950-37-8
反应条件:1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol; 0.05 Mpa,Rt -> 60 °C; 3 H,50 - 60 °C1.2 Reagents: Ammonia Solvents: Methanol; Ph 8 - 9
标题:Method For Synthesizing 4-Methyl-7H-Pyrrolo[2,3-D]Pyrimidine From 2,4-Dichloro-7H-Pyrrolo[2,3-D]Pyrimidine
参考文献:China]

3680-69-1 = 945950-37-8
反应条件:1.1 Catalysts: Dichloro[1,1′-Bis(Diphenylphosphino)Ferrocene]Palladium(Ii) Dichloromethane Addu... Solvents: Toluene; 10 Min,Rt1.2 Solvents: Diethyl Ether; Rt; Overnight,55 °C; -70 °C -> -80 °C1.3 Reagents: Ammonium Chloride; -80 °C1.4 Reagents: Hydrochloric Acid Solvents: Water1.5 Reagents: Sodium Bicarbonate Solvents: Water; Ph 7 - 8
标题:Pyrrolopyrimidines And Pyrrolopyridines As Protein Kinase Modulators Useful In The Treatment Of Protein Kinase-Mediated Diseases
参考文献:World Intellectual Property Organization]

3680-69-1 = 945950-37-8
反应条件:1.1 Catalysts: Dichloro[1,1′-Bis(Diphenylphosphino)Ferrocene]Palladium(Ii) Dichloromethane Addu... Solvents: Toluene; 10 Min,Rt1.2 Rt; Rt -> 60 °C; 3 H,60 °C; Overnight,Rt1.3 Reagents: Benzenesulfonyl Chloride Solvents: Water; Ph 5
标题:Preparation Of Substituted Phenyl(1H-Pyrrolo[2,3-B]Pyridin-3-Yl)Methanones And Phenyl(7H-Pyrrolo[2,3-D]Pyrimidin-5-Yl)Methanones As Protein Kinase Modulators,Particularly Inhibitors Of Raf Protein Kinases
参考文献:World Intellectual Property Organization]

3680-69-1 = 945950-37-8
反应条件:1.1 Reagents: Sodium Hydride Solvents: Tetrahydrofuran; 30 Min,0 - 15 °C1.2 Reagents: Tert-Butyldimethylsilyl Chloride Solvents: Tetrahydrofuran; 1 - 2 H,0 - 15 °C; 15 °C -> -10 °C1.3 Catalysts: Iron(Iii) Acetylacetonate Solvents: Tetrahydrofuran; 2 H,15 - 30 °C1.4 Reagents: Ammonium Chloride Solvents: Water; < 10 °C1.5 Reagents: Ammonium Hydroxide Solvents: Water; 16 H,15 - 40 °C
标题:Process And Intermediates For Preparing Baricitinib
参考文献:World Intellectual Property Organization]

3680-69-1 = 945950-37-8
反应条件:1.1 Reagents: Sodium Hydride Solvents: Tetrahydrofuran; 30 Min,0 - 15 °C1.2 Reagents: Tert-Butyldimethylsilyl Chloride Solvents: Tetrahydrofuran; 1 - 2 H,0 - 15 °C; 15 °C -> -10 °C1.3 Catalysts: Iron(Iii) Acetylacetonate Solvents: Tetrahydrofuran; < 15 °C; 2 H,15 - 30 °C1.4 Reagents: Ammonium Chloride Solvents: Water; < 10 °C1.5 Reagents: Ammonium Hydroxide Solvents: Methanol,Water; 16 H,15 - 40 °C
标题:Industrial Process Synthesis Of Itacitinib Intermediate Salts Toward Jak Inhibitors
参考文献:World Intellectual Property Organization]

2697704-48-4 = 945950-37-8
反应条件:1.1 Reagents: Potassium Hydroxide Solvents: Methanol; 1 H,Rt1.2 Reagents: Hydrochloric Acid Solvents: Water; Ph 6 - 7,Rt
标题:Method For Preparing Jak Inhibitor Key Intermediate
参考文献:World Intellectual Property Organization]

3680-69-1 = 945950-37-8
反应条件:1.1 Catalysts: [1,1′-Bis(Diphenylphosphino)Ferrocene]Dichloropalladium Solvents: Tetrahydrofuran; 0.5 H,Rt; Rt -> 0 °C1.2 Solvents: Diethyl Ether; < 0 °C; 2 H,0 °C -> 65 °C; 65 °C -> 0 °C1.3 Reagents: Hydrochloric Acid Solvents: Water; < 0 °C1.4 Reagents: Sodium Bicarbonate; Ph 6
标题:Process For Synthesis Of Ruxolitinib
参考文献:World Intellectual Property Organization]

3680-69-1 = 945950-37-8
反应条件:1.1 Catalysts: Iron Chloride (Fecl3) Solvents: Tetrahydrofuran,N-Methyl-2-Pyrrolidone; 2 H,0 °C
标题:Novel 6-Substituted 7-Deazapurines And Corresponding Nucleosides As Medicaments
参考文献:World Intellectual Property Organization]

3680-69-1 = 945950-37-8
反应条件:1.1 Catalysts: [1,1′-Bis(Diphenylphosphino)Ferrocene]Dichloropalladium Solvents: Tetrahydrofuran,Water; 25 °C; 16 H,60 °C1.2 Reagents: Sodium Bicarbonate Solvents: Water
标题:Preparation Of Fused Heterocyclic Compounds As Irreversible Inhibitors Of Menin-Mll Interaction
参考文献:World Intellectual Property Organization]

2761879-42-7 = 945950-37-8
反应条件:1.1 Reagents: Sodium Hydroxide Solvents: Water; Ph 7.5 - 8.5,Rt
标题:Process For Preparation Of Ruxolitinib And Intermediates Thereof
参考文献:India]

3680-69-1 + 823-96-1 = 945950-37-8
反应条件:1.1 Catalysts: Palladium
标题:Treatment Of Subjects Suffering From Having Cholangiocarcinoma Using A Tyrosine Kinase Lck Inhibitor
参考文献:World Intellectual Property Organization]

3680-69-1 = 945950-37-8
反应条件:1.1 Catalysts: Tetrakis(Triphenylphosphine)Palladium Solvents: Toluene,Tetrahydrofuran; Overnight,Reflux; Reflux -> 0 °C1.2 Reagents: Ammonium Chloride Solvents: Water; 0 °C
标题:Preparation Of N-(Pyrimidinylthiazolylphenyl) Sulfonamides As Lim Kinase Inhibitors
参考文献:World Intellectual Property Organization]

3680-69-1 = 945950-37-8
反应条件:1.1 Catalysts: Dichloro[1,1′-Bis(Diphenylphosphino)Ferrocene]Palladium(Ii) Dichloromethane Addu... Solvents: Toluene; 10 Min1.2 Solvents: Diethyl Ether; Overnight,55 °C; 55 °C -> -80 °C1.3 Reagents: Ammonium Chloride; -80 - -70 °C1.4 Reagents: Hydrochloric Acid Solvents: Water1.5 Reagents: Sodium Bicarbonate Solvents: Water; Ph 7 - 8
标题:Preparation Of Azaindole Compounds And Methods For Kinase Modulation,And Indications Therefor
参考文献:World Intellectual Property Organization

4-氯-7-甲苯磺酰基-7H-吡咯[2,3-D]嘧啶置于potassium Hydroxide体系中,用四氢呋喃,甲醇作为反应溶剂,化学反应 3.0H,反应生成 4-甲基-7H-吡咯并[2,3-D]嘧啶
参考文献:一种jak抑制剂关键中间体的制备方法
标题:一种jak抑制剂关键中间体的制备方法
摘要:本发明公开了一种jak抑制剂关键中间体的制备方法,包括以下步骤:步骤a,将原料4‑氯‑7H‑吡咯‑[2.3‑d]‑嘧啶的氨基进行保护合成4‑氯‑7‑对甲苯磺酰基‑吡咯‑[2.3‑d]‑嘧啶;步骤b,将4‑氯‑7‑对甲苯磺酰基‑吡咯‑[2.3‑d]‑嘧啶与甲基化试剂反应合成4‑甲基‑7‑对甲苯磺酰基‑吡咯‑[2.3‑d]‑嘧啶;步骤c,将4‑甲基‑7‑对甲苯磺酰基‑吡咯‑[2.3‑d]‑嘧啶进行脱保护合成4‑甲基‑7H‑吡咯‑[2.3‑d]‑嘧啶.根据本发明实施例的jak抑制剂关键中间体的制备方法,原料市场价格价廉且易得,生产成本低,而且该合成方法的每一步都是常规反应,不使用高危险性的试剂,操作简单,由于先进行保护,减少了格式试剂的用量及避免了c‑n双分子偶联杂质的反应生成,提高了产品纯度,使后处理更容易.

专利信息

专利号:US-10562904-B2
优先权日:2015-12-31
标题:Synthesis process of ruxolitinib
发明人：ZHANG XIQUAN; ZHANG AIMING; ZHOU ZHOU; YANG LEILEI; YAO HUADONG; ZHU XUEYAN; WANG HUBO
权利人:CHIA TAI TIANQING PHARMACEUTICAL GROUP CO LTD
摘要:The present application falls within the field of drug synthesis, and in particular, the present application relates to a method for preparing ruxolitinib, and a method for preparing the intermediate and relevant intermediates used. The method comprises reacting a compound of formula II with a compound of formula IV or a salt thereof to obtain a compound of formula III, and then subjecting the compound of formula III to an acyl halogenation reaction, an amidation reaction, and a reaction dehydrating an amide to form a cyano group or removing the protecting group to prepare ruxolitinib. The method has the characteristics of brief steps, a high stereoselectivity, a high utilization ratio of atoms, mild reaction conditions and convenient post treatment. The method avoids using expensive asymmetric reaction catalysts, and is suitable for industrial production.

专利号:WO-2011050245-A1
优先权日:2009-10-23
标题:Bicyclic heteroaryls as kinase inhibitors
发明人：FENG YANGBO; CHEN YEN TING; SESSIONS HAMPTON; MISHRA JITENDRA K; CHOWDHURY SARWAT; YIN YAN; LOGRASSO PHILIP; LUO JUN-LI; BANNISTER THOMAS; SCHROETER THOMAS
权利人:FENG YANGBO; CHEN YEN TING; SESSIONS HAMPTON; MISHRA JITENDRA K; CHOWDHURY SARWAT; YIN YAN; LOGRASSO PHILIP; LUO JUN-LI; BANNISTER THOMAS; SCHROETER THOMAS
摘要:The invention is directed to heteroaryl compounds useful as inhibitors of various kinase enzymes. In various embodiments, the invention provides a heteroaryl compound having inhibitory bioactivity with respect to a Rho kinase, an AKT kinase, a p70S6K kinase, a LIM kinase, an IKK kinase, a Flt kinase, an Aurora kinase, or a Src kinase, or any combination thereof. Compounds of the invention include bicyclic heteroaryl compounds of formula (I), which can contain a bridging nitrogen atom at a ring junction. The invention further provides methods of synthesis of compounds of the invention, pharmaceutical compositions, pharmaceutical combinations, and methods of treatment of malconditions using compounds of the invention.

专利号:US-2019023712-A1
优先权日:2015-12-31
标题 :Synthesis process of ruxolitinib

专利号:US-11014926-B2
优先权日:2015-10-29
标题 :Pyrrolo-, pyrazolo-, imidazo-pyrimidine and pyridine compounds that inhibit MNK1 and MNK2
发明人：SPRENGELER PAUL A; REICH SIEGFRIED H; ERNST JUSTIN T; WEBBER STEPHEN E
权利人:EFFECTOR THERAPEUTICS INC
摘要:The present invention provides synthesis, pharmaceutically acceptable formulations and uses of compounds in accordance with Formula I. or a stereoisomer, tautomer or pharmaceutically acceptable salt thereof. n nFor Formula I compounds A 1 , A 2 . A 3 , A 4 , A 5 , A 6 , A 7 , W 1 , R 1 , R 2 , R 3 , R 4 , R 5a , R 5b , R 6 , R 7 , R 7a , R 7b , R 8 , R 8a , R 8b , R 9 , R 9a , R 9b and R 10 and subscripts â€œmâ€? and â€œnâ€? are as defined in the specification. The inventive Formula I compounds are inhibitors of Mnk and find utility in any number of therapeutic applications, including but not limited to treatment of inflammation and various cancers.

专利号:EP-3398952-B1
优先权日:2015-12-31
标题 :Synthesis process of ruxolitinib

专利号:EP-3398952-A1
优先权日:2015-12-31
标题:Synthesis process of ruxolitinib