4,6-Dichloro-2-(methylthio)pyrimidine → 4-Chloro-6-methoxy-2-(methylthio)pyrimidine

HRID 1862314Notes

Reaction equation

HRID 1862314 reaction equation
[CH3:1][OH:2].C[O-].[Na+].[Cl:6][C:7]1[CH:12]=[C:11](Cl)[N:10]=[C:9]([S:14][CH3:15])[N:8]=1>CN(C)C=O>[Cl:6][C:7]1[CH:12]=[C:11]([O:2][CH3:1])[N:10]=[C:9]([S:14][CH3:15])[N:8]=1

Participants

4

Reactant 2

HCID 805314,6-Dichloro-2-(methylthio)pyrimidineHCID 23694274Sodium methanolate methanol

Product 1

HCID 98369994-Chloro-6-methoxy-2-(methylthio)pyrimidineYield 83.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.86 g of 28% sodium methoxide methanol solution was added dropwise over 20 minutes to a solution of 3.9 g of 4,6-dichloro-2-methylthiopyrimidine in 20 ml of N,N-dimethylformamide at 0° C. Then the mixture was stirred at room temperature for 7 hours. 20 g of ice was added to the mixture, then white precipitate was collected by suction filtration, and the solid was washed with water. The solid was dissolved in ethyl acetate, washed with saturated saline, dried over anhydrous magnesium sulfate, and concentrated to obtain 3.18 g of 4-chloro-6-methoxy-2-methylthiopyrimidine.

Workup

  1. filtrationwhite precipitate was collected by suction filtration
  2. washthe solid was washed with water
  3. dissolutionThe solid was dissolved in ethyl acetate
  4. washwashed with saturated saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e2cfc195e2d5455ca8a6d02a82ab5110
Source dataset
uspto-grants-2003_03
Patent number
US06537948B1

Reaction notes

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