Calcium Carbonate → 2-Amino-5-bromo-4-phenylpyrimidine

Participants

Reaction Steps

Following the method of Ziegler and Clementon (U.S. Pat. No. 2,609,372), to a stirred suspension of 5.0 g (29.2 mmol) 2-amino-4-phenylpyrimidine and 1.46 g (14.6 mmol) CaCO3 in 30 ml water at 50° C. was added dropwise 1.65 ml (32.2 mmol) bromine and stirring continued for 30 minutes. The reaction mixture was then made basic by addition of ammonium hydroxide solution and extracted three times with ethyl acetate. The combined organic phases were washed with saturated brine, dried over sodium sulfate, and concentrated in vacuo. Recrystallisation from ethanol afforded 3.27 g (45%) 5-bromo-4-phenyl-pyrimidin-2-ylamine as a green crystalline solid. EI-MS m/e (%): 251 (M{81Br}+, 64), 249 (M{79Br}+, 64), 170 ([M—Br]+, 100).

Provenance & Evidence