Water → HCID 54112985, compound

HRID 354013Notes

Reaction equation

HRID 354013 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:24]=[C:25]([Cl:27])[CH:26]=1)[CH2:5][NH:6][C:7]([C:9]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])=[CH:13][N:12]=[C:11]([S:22][CH3:23])[N:10]=1)=[O:8].[CH3:28]N(C)C=O.CI.O>[Cl-].[Na+].O.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:24]=[C:25]([Cl:27])[CH:26]=1)[CH2:5][N:6]([CH3:28])[C:7]([C:9]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])=[CH:13][N:12]=[C:11]([S:22][CH3:23])[N:10]=1)=[O:8]

Participants

7

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 6328Methyl iodideHCID 53997340HCID 53997340, compound

Product 1

HCID 54112985HCID 54112985, compoundYield 92.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 0.6 g (1.43 mmol) methylsulfanyl-5-o-tolyl-pyrimidine-4-carboxylic acid 3,5-dichloro-benzylamide in 10 ml N,N-dimethylformamide 0.073 g (1.85 mmol) sodiumhydride (60% dispersion in mineral oil) was added and the reaction stirred for 1 h. After the addition of 0.14 ml 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 and 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, CH2Cl2/ethyl acetate 40:1) to give 0.57 g (92%) 2-methylsulfanyl-5-o-tolyl-pyrimidine-4-carboxylic acid (3,5-dichloro-benzyl)-methyl-amide as a colorless oil, MS (ISP): 432.2, 434.2 (M+H+).

Workup

  1. stirringthe reaction mixture was stirred for 3 hrs at RT
  2. customThe phases were separated
  3. washthe aqueous layer washed twice with 50 ml CH2Cl2
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by chromatography (SiO2, CH2Cl2/ethyl acetate 40:1)

Sources & evidence

ORD record
ord-358dbd7cefb3413c9f6b38517e6cbc4e
Source dataset
uspto-grants-2004_06
Patent number
US06756380B1

Reaction notes

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