Water → HCID 86585536, compound

HRID 1005973Notes

Reaction equation

HRID 1005973 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:25]=[C:26]([Cl:28])[CH:27]=1)[CH2:5][NH:6][C:7]([C:9]1[C:10]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[CH3:24])=[N:11][C:12]([S:15][CH3:16])=[N:13][CH:14]=1)=[O:8].[CH3:29]N(C)C=O.CI.O>[Cl-].[Na+].O.C(Cl)Cl>[Cl:28][C:26]1[CH:25]=[C:4]([CH:3]=[C:2]([Cl:1])[CH:27]=1)[CH2:5][N:6]([CH3:29])[C:7]([C:9]1[C:10]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[CH3:24])=[N:11][C:12]([S:15][CH3:16])=[N:13][CH:14]=1)=[O:8]

Participants

7

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 6328Methyl iodideHCID 69922686HCID 69922686, compound

Product 1

HCID 86585536HCID 86585536, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 0.6 g (1.8 mmol) 2-methylsulfanyl-4-o-tolyloxy-pyrimidine-5-carboxylic acid 3,5-dichloro-benzylamide in 20 ml N,N-dimethylformamide 0.096 g (2.4 mmol) sodiumhydride (60% dispersion in mineraloil) was added and the mixture stirred for 1 h. After the addition of 0.18 ml (2.9 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, and the aqueous layer extracted 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 19:1) to give 0.5 g (61%) 2-methylsulfanyl-4-o-tolyloxy-pyrimidine-5-carboxylic acid (3,5-dichloro-benzyl)-methyl-amide as a light yellow oil, MS (EI): 447.1 (M+).

Workup

  1. stirringthe reaction mixture was stirred for 3 hrs
  2. customat RT
  3. customThe phases were separated
  4. extractionthe aqueous layer extracted 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, CH2Cl2/ethyl acetate 19:1)

Sources & evidence

ORD record
ord-c9bcb324e8cd4e1a8d8f553e764fe99c
Source dataset
uspto-grants-2004_09
Patent number
US06787539B2

Reaction notes

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