Water → HCID 54437820, compound

HRID 353993Notes

Reaction equation

HRID 353993 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:4]=[C:5]([CH:19]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:21]=1)[CH2:6][NH:7][C:8]([C:10]1[C:15]([Br:16])=[CH:14][N:13]=[C:12]([S:17][CH3:18])[N:11]=1)=[O:9].[CH3:28]N(C)C=O.CI.O>[Cl-].[Na+].O.C(Cl)Cl>[F:25][C:22]([F:24])([F:23])[C:20]1[CH:19]=[C:5]([CH:4]=[C:3]([C:2]([F:1])([F:26])[F:27])[CH:21]=1)[CH2:6][N:7]([CH3:28])[C:8]([C:10]1[C:15]([Br:16])=[CH:14][N:13]=[C:12]([S:17][CH3:18])[N:11]=1)=[O:9]

Participants

7

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 6328Methyl iodideHCID 54035087HCID 54035087, compound

Product 1

HCID 54437820HCID 54437820, compoundYield 77.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 4.40 g (9.28 mmol) 5-bromo-2-methylsulfanyl-pyrimidine-4-carboxylic acid 3,5-bis-trifluoromethyl-benzylamide in 50 ml N,N-dimethylformamide 0.48 g (12.06 mmol) sodiumhydride (60% dispersion in mineral oil) was added and the reaction mixture stirred for 1 hr. After the addition of 0.92 ml (14.85 mmol) methyl iodide at 0°, the reaction mixture was stirred for 3 hrs. at RT. The reaction mixture was distributed between 100 ml H2O, 100 ml brine and 100 ml CH2Cl2. The phases were separated, the aqueous layer washed twice with 100 ml CH2Cl2. The combined organic layers were dried (MgSO4), filtered and evaporated. The residue was purified by chromatography (SiO2, CH2Cl2/ethyl acetate 40:1) to give 3.50 g (77%) 5-bromo-2-methylsulfanyl-pyrimidine-4-carboxylic acid (3,5-bis-trifluoromethyl-benzyl)-methyl-amide as a colorless oil.

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 100 ml CH2Cl2
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by chromatography (SiO2, CH2Cl2/ethyl acetate 40:1)

Sources & evidence

ORD record
ord-12282d5029824f2d8def52888ab4f06b
Source dataset
uspto-grants-2004_06
Patent number
US06756380B1

Reaction notes

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