Dimethylformamide → 6-Methoxy-4-{1-(methoxycarbonyl)ethoxy}-2-methylthiopyrimidine

HRID 1862315Notes

Reaction equation

HRID 1862315 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:19][CH3:20])(=[O:18])[CH:15]([CH3:17])[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][CH:15]([C:14]([O:19][CH3:20])=[O:18])[CH3:17])[CH:9]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11040Methyl LactateHCID 24758Sodium hydrideHCID 98369994-Chloro-6-methoxy-2-(methylthio)pyrimidine

Product 1

HCID 186192486-Methoxy-4-{1-(methoxycarbonyl)ethoxy}-2-methylthiopyrimidineYield 69.6%

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, 1.13 g of methyl lactate 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 1.5 g of 6-methoxy-4-{1-(methoxycarbonyl)ethoxy}-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-dd68a39bfde14b5abc49d00d15ae2e1b
Source dataset
uspto-grants-2003_03
Patent number
US06537948B1

Reaction notes

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