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ChemicalBook CAS DataBase List 2-Chloro-4,5-diaminopyrimidine
14631-08-4

2-Chloro-4,5-diaminopyrimidine synthesis

1synthesis methods
A mixture of 2-chloro-5-nitropyrimidin-4-amine (1.0 g, 5.7 mmol) and SnCl2·2H2O (5.2 g, 22.9 mmol) in EtOH (55 mL) under N2 was heated to 80 °C and stirred for two hours. The mixture was then concentrated under reduced pressure. EtOAc and Celite were added to the residue, and the mixture was basified with saturated Na2CO3 (aq.) to pH 9- 10. The mixture was filtered through a pad of Celite and washed with EtOAc. The organic layer was separated, washed with brine, dried (Na2SO4), and concentrated in a vacuum. The residue was purified on ISCO (20 g silica gel column, EtOAc/hexanes 0~100 per cent) to give 2-Chloro-4,5-diaminopyrimidine (0.41 g 49 per cent).
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Yield: 54.5%

Reaction Conditions:

with water;iron;ammonium chloride in ethanol at 100; for 4 h;

Steps:

21 Synthesis of Compound 21-3
To a solution of compound 21-2 (20 g, 114.6 mmol) in EtOH/H2O (4/1, 400 mL) was added iron powder (64 g, 1146 mmol) and NH4Cl (aq., 62 g, 1146 mmol), the reaction solution was stirred at 100° C. for 4 h, followed by filtration. The filter cake was washed with MeOH (10 mL×3) and the filtrate was concentrated to give compound 21-3 (9 g, Yield 54.5%) as yellow solid.

References:

Hubei Bio-Pharmaceutical Industrial Technological Institute Inc.;Humanwell Healthcare (Group) Co., Ltd.;Wang, Xuehai;Wu, Chengde;Xu, Yong;Shen, Chunli;Li, Li'e;Hu, Guoping;Yue, Yang;Li, Jian;Guo, Diliang;Shi, Nengyang;Huang, Lu;Chen, Shuhui;Tu, Ronghua;Yang, Zhongwen;Zhang, Xuwen;Xiao, Qiang;Tian, Hua;Yu, Yanping;Chen, Hailiang;Sun, Wenjie;He, Zhenyu;Shen, Jie;Yang, Jing;Tang, Jing;Zhou, Wen;Yu, Jing;Zhang, Yi;Liu, Quan US2017/313683, 2017, A1 Location in patent:Paragraph 0544

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