Water → HCID 56982997, compound

HRID 354015Notes

Reaction equation

HRID 354015 reaction equation
[C:1]([O:5][C:6](=[O:23])[NH:7][C:8]1[C:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH3:20])=[CH:12][N:11]=[C:10]([S:21][CH3:22])[N:9]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:24]N(C)C=O.CI.O>[Cl-].[Na+].O.C(Cl)Cl>[C:1]([O:5][C:6](=[O:23])[N:7]([CH3:24])[C:8]1[C:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH3:20])=[CH:12][N:11]=[C:10]([S:21][CH3:22])[N:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 6328Methyl iodideHCID 57238032HCID 57238032, compound

Product 1

HCID 56982997HCID 56982997, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 2.45 g (7.40 mmol) (2-methylsulfanyl-5-o-tolyl-pyrimidin-4-yl)-carbamic acid tert.-butyl ester in 30 ml N,N-dimethylformamide 0.44 g (11.09 mmol) sodiumhydride (60% dispersion in mineraloil) was added and the reaction mixture stirred for 1 hr. After the addition of 0.74 ml (11.83 mmol) methyl iodide at 0°, the reaction mixture was stirred for 3 hrs. The reaction mixture was distributed between 75 ml H2O, 75 ml brine and 75 ml CH2Cl2. The phases were separated, the aqueous layer washed twice with 75 ml CH2Cl2. The combined organic layers were dried (Na2SO4), filtered and evaporated. The residue was purified by chromatography (SiO2, CH2Cl2/ethyl acetate 19:1) to give 2.50 g (98%) methyl-(2-methylsulfanyl-5-o-tolyl-pyrimidin-4-yl)-carbamic acid tert.-butyl ester as a colorless oil, MS (TSP): 345 (M+).

Workup

  1. stirringthe reaction mixture was stirred for 3 hrs
  2. customThe phases were separated
  3. washthe aqueous layer washed twice with 75 ml CH2Cl2
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by chromatography (SiO2, CH2Cl2/ethyl acetate 19:1)

Sources & evidence

ORD record
ord-6a6f42933d00438da495c2c8f3474be7
Source dataset
uspto-grants-2004_06
Patent number
US06756380B1

Reaction notes

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