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

HRID 1355806Notes

Reaction equation

HRID 1355806 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:4][N:3]=1.C([O-])([O-])=O.[Ca+2].[Br:19]Br.[OH-].[NH4+]>O>[Br:19][C:5]1[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:7][C:2]([NH2:1])=[N:3][CH:4]=1

Participants

6

Reactant 4

HCID 10112Calcium CarbonateHCID 14923Ammonium HydroxideHCID 24408BromineHCID 5987772-Amino-4-phenylpyrimidine

Product 1

HCID 113456882-Amino-5-bromo-4-phenylpyrimidineYield 45%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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).

Workup

  1. extractionextracted three times with ethyl acetate
  2. washThe combined organic phases were washed with saturated brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customRecrystallisation from ethanol

Sources & evidence

ORD record
ord-a956721f43eb40b3b9865ccbfaf4e8c6
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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