Water → HCID 17961392, compound

HRID 650620Notes

Reaction equation

HRID 650620 reaction equation
[F:1][C:2]([F:31])([F:30])[C:3]1[CH:4]=[C:5]([CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:25]=1)[CH2:6][NH:7][C:8]([C:10]1[C:11]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:12][C:13]([CH3:16])=[N:14][CH:15]=1)=[O:9].[CH3:32]N(C)C=O.CI.O>[Cl-].[Na+].O.C(Cl)Cl>[F:31][C:2]([F:1])([F:30])[C:3]1[CH:4]=[C:5]([CH:23]=[C:24]([C:26]([F:27])([F:28])[F:29])[CH:25]=1)[CH2:6][N:7]([CH3:32])[C:8]([C:10]1[C:11]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[N:12][C:13]([CH3:16])=[N:14][CH:15]=1)=[O:9]

Participants

7

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 6328Methyl iodideHCID 54007509HCID 54007509, compound

Product 1

HCID 17961392HCID 17961392, compoundYield 72.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 0.67 g (1.52 mmol) methyl-4-phenyl-pyrimidine-5-carboxylic acid 3,5-bis-trifluoromethyl-benzylamide in 10 ml N,N-dimethylformamide 0.08 g (1.98 mmol) sodiumhydride (60% dispersion in mineral oil) was added and the reaction mixture stirred for 1 hr. After the addition of 0.15 ml (2.4 mmol) methyl iodide at 0°, the reaction mixture was stirred for 3 hrs. at RT. The reaction mixture was distributed between 50 ml H2O, 50 ml brine and 50 ml CH2Cl2. The phases were separated, the aqueous layer washed twice with 50 ml CH2Cl2. The combined organic layers were dried (MgSO4), filtered and evaporated. The residue was purified by chromatography (SiO2, ethyl acetate/hexane 4:1) to give 0.50 g (72%) 2-methyl-4-phenyl-pyrimidine-5-carboxylic acid (3,5-bis-trifluoromethyl-benzyl)-methyl-amide as a colorless oil, MS (EI): 453 (M+).

Workup

  1. stirringthe reaction mixture was stirred for 3 hrs
  2. customat RT
  3. customThe phases were separated
  4. washthe aqueous layer washed twice with 50 ml CH2Cl2
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by chromatography (SiO2, ethyl acetate/hexane 4:1)

Sources & evidence

ORD record
ord-0d5c515194f7412c886dbd6d03e10f6d
Source dataset
uspto-grants-2001_08
Patent number
US06274588B1

Reaction notes

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