Ammonia → HCID 54002387, compound

HRID 650634Notes

Reaction equation

HRID 650634 reaction equation
[F:1][C:2]([F:36])([F:35])[C:3]1[CH:4]=[C:5]([CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=1)[CH2:6][N:7]([CH3:27])[C:8]([C:10]1[C:11]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[Br:26])=[N:12][C:13](S(C)(=O)=O)=[N:14][CH:15]=1)=[O:9].[NH3:37]>CN(C)C=O>[F:1][C:2]([F:36])([F:35])[C:3]1[CH:4]=[C:5]([CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=1)[CH2:6][N:7]([CH3:27])[C:8]([C:10]1[C:11]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[Br:26])=[N:12][C:13]([NH2:37])=[N:14][CH:15]=1)=[O:9]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 54285316HCID 54285316, compound

Product 1

HCID 54002387HCID 54002387, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.42 g (0.7 mmol) 4-(2-bromo-phenyl)-2-methylsulfonyl-pyrimidine-5-carboxylic acid (3,5-bis-trifluoromethyl-benzyl)-methyl-amide in 30 ml N,N-dimethylformamide a stream of NH3 was introduced during 10 Min. The reaction solution was stirred for 4 hrs. The solvent was evaporated and the residue distributed between 20 ml CH2Cl2 and 20 ml H2O. The aqueous phase was extracted twice with 30 ml CH2Cl2. The combined organic layers were dried (MgSO4), filtered and evaporated. The residue was purified by chromatography (SiO2, CH2Cl2/MeOH/NH4OH 140:10:1) to give 0.29 g (77%) 2-amino-4-(2-bromo-phenyl)-pyrimidine-5-carboxylic acid (3,5-bis-trifluoromethyl-benzyl)-methyl-amide as a white foam, MS (ISP): 535.1, 533.1 (M+H+).

Workup

  1. customThe solvent was evaporated
  2. extractionThe aqueous phase was extracted twice with 30 ml CH2Cl2
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by chromatography (SiO2, CH2Cl2/MeOH/NH4OH 140:10:1)

Sources & evidence

ORD record
ord-31c2c87e8c9948c582aea414607d2de3
Source dataset
uspto-grants-2001_08
Patent number
US06274588B1

Reaction notes

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