Dimethylformamide → 6-Methoxy-4-(methoxycarbonyl)methoxy-2-methylthiopyrimidine

HRID 1862311Notes

Reaction equation

HRID 1862311 reaction equation
[H-].[Na+].Cl[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[N:7]=[C:6]([S:12][CH3:13])[N:5]=1.[C:14]([O:18][CH3:19])(=[O:17])[CH2:15][OH:16].CN(C)C=O>O>[CH3:11][O:10][C:8]1[N:7]=[C:6]([S:12][CH3:13])[N:5]=[C:4]([O:16][CH2:15][C:14]([O:18][CH3:19])=[O:17])[CH:9]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 66774Methyl GlycolateHCID 98369994-Chloro-6-methoxy-2-(methylthio)pyrimidine

Product 1

HCID 186191496-Methoxy-4-(methoxycarbonyl)methoxy-2-methylthiopyrimidineYield 59.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.4 g of sodium hydride was added to a mixture of 1.59 g of 4-chloro-6-methoxy-2-methylthiopyrimidine, 0.98 g of methyl glycolate and 10 ml of N,N-dimethylformamide at 0° C. The mixture was stirred at room temperature for 5 hours, then, the reaction solution was poured into water, and extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 1.22 g of 6-methoxy-4-(methoxycarbonyl)methoxy-2-methylthiopyrimidine.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2731ef37d29f49258025de724c9914ec
Source dataset
uspto-grants-2003_03
Patent number
US06537948B1

Reaction notes

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