Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 330786-24-8, name is 3-(4-Phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine. A new synthetic method of this compound is introduced below., Safety of 3-(4-Phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
Example 1-1 : Preparation of (i?)-3-(4-phenoxyphenyl)-l-(pyrrolidin-3-yl)-lH-pyrazolo[3,4- ]pyrimidin-4-amine (Compound A)[00367] To a mixture of 4-amino-3-(4-phenoxyphenyl)-lH-pyrazolo[3,4-d]pyrimidine (45.50 g, 150 mmol, 1.0 eq), (S)-pyrrolidin-3-ol (bought from CNH, 51.95g, 277.5 mmol, 1.85 eq) and Ph3P (72.79g, 277.5 mmol, 1.85 eq) in THF (400 mL) at rt was added DIAD (57.6 mL, 292.5mmol, 1.95 eq) dropwise over 1.5 h. The mixture was stirred another 30 min and concentrated HC1 solution (100 mL) was added dropwise over 30 min. The mixture was stirred overnight at rt. The mixture was then heated to 50 C for 1 h to push the de-Boc to completion. THF was removed by rotavap. The crude was diluted with toluene and water. The aqueous solution was further washed with EtOAc and toluene. MeOH (70 mL, 10% v/v to the aqueous solution) was added followed by KOH solution (100 g in 100 mL water). The mixture became warm and precipitate immediately formed. The mixture was cooled in a 4 C fridge for 2 h and filtered. The solid was washed with water, air-dried and then dried under high- vac for 3 days. Yield 49.45 g (89%), HPLC purity 95%.
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Reference:
Patent; PHARMACYCLICS, INC.; CHEN, Wei; LOURY, David, J.; MODY, Tarak, D.; WANG, Longcheng; WO2013/10136; (2013); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia