Ammonia → HCID 53709744, compound

HRID 353997Notes

Reaction equation

HRID 353997 reaction equation
[F:1][C:2]([F:35])([F:34])[C:3]1[CH:4]=[C:5]([CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:29]=1)[CH2:6][N:7]([CH3:26])[C:8]([C:10]1[C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:14][N:13]=[C:12](S(C)(=O)=O)[N:11]=1)=[O:9].[NH3:36].O>CN(C)C=O>[F:1][C:2]([F:35])([F:34])[C:3]1[CH:4]=[C:5]([CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:29]=1)[CH2:6][N:7]([CH3:26])[C:8]([C:10]1[C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:14][N:13]=[C:12]([NH2:36])[N:11]=1)=[O:9]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 962WaterHCID 54161888HCID 54161888, compound

Product 1

HCID 53709744HCID 53709744, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.3 g (0.58 mmol) 2-methanesulfonyl-5-phenyl-pyrimidine-4-carboxylic acid (3,5-bis-trifluoromethyl-benzyl)-methyl-amide in 20 ml N,N-dimethylformamide a stream of NH3-Gas was introduced during 10 Min. The reaction mixture was poured onto 100 ml H2O. The aqueous layer was extracted three times with 50 ml CH2Cl2, the combined organic layers dried (MgSO4), filtered and evaporated. The residue was purified by chromatography (SiO2, CH2Cl2/MeOH/NH4OH 140:10:1) to give 0.17 g (65%) 2-amino-5-phenyl-pyrimidine-4-carboxylic acid (3,5-bis-trifluoromethyl-benzyl)-methyl-amide as a off-white solid, m.p. 181.5-182.5°.

Workup

  1. extractionThe aqueous layer was extracted three times with 50 ml CH2Cl2
  2. dry with materialthe combined organic layers dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by chromatography (SiO2, CH2Cl2/MeOH/NH4OH 140:10:1)

Sources & evidence

ORD record
ord-bd35550429324b67b0706588f18c8c1a
Source dataset
uspto-grants-2004_06
Patent number
US06756380B1

Reaction notes

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