Water → HCID 53758416, compound

HRID 353999Notes

Reaction equation

HRID 353999 reaction equation
[F:1][C:2]([F:26])([F:25])[C:3]1[CH:4]=[C:5]([CH:18]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:20]=1)[CH2:6][NH:7][C:8]([C:10]1[C:15]([Br:16])=[CH:14][N:13]=[C:12]([CH3:17])[N:11]=1)=[O:9].[CH3:27]N(C)C=O.CI.O>[Cl-].[Na+].O.C(Cl)Cl>[F:22][C:21]([F:24])([F:23])[C:19]1[CH:18]=[C:5]([CH:4]=[C:3]([C:2]([F:1])([F:25])[F:26])[CH:20]=1)[CH2:6][N:7]([CH3:27])[C:8]([C:10]1[C:15]([Br:16])=[CH:14][N:13]=[C:12]([CH3:17])[N:11]=1)=[O:9]

Participants

7

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 6328Methyl iodideHCID 53949364HCID 53949364, compound

Product 1

HCID 53758416HCID 53758416, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 2.28 g (5 mmol) 5-bromo-2-methyl-pyrimidine-4-carboxylic acid 3,5-bis-trifluoromethyl-benzylamide in 20 ml N,N-dimethylformamide 0.26 g (5.5 mmol) sodiumhydride (60% dispersion in mineral oil) was added and the reaction mixture stirred for 1 hr. After the addition of 0.4 ml (6.5 mmol) methyl iodide at 0°, the reaction mixture was stirred for 3 hrs. at RT. The reaction mixture was distributed between 80 ml H2O, 80 ml brine and 80 ml CH2Cl2. The phases were separated, the aqueous layer washed twice with 80 ml CH2Cl2. The combined organic layers were dried (MgSO4), filtered and evaporated. The residue was purified by chromatography (SiO2, CH2Cl2/MeOH 19:1) to give 1.98 g (87%) 5-bromo-2-methyl-pyrimidine-4-carboxylic acid (3,5-bis-trifluoromethyl-benzyl)-methyl-amide as a waxy solid.

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 80 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/MeOH 19:1)

Sources & evidence

ORD record
ord-98c432857070428ba60ac9b03c360ea7
Source dataset
uspto-grants-2004_06
Patent number
US06756380B1

Reaction notes

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