Sodium hydride → 4,6-Bis-(1,1-dimethylethyl)-5-[(2-methoxyethoxy) methoxy]-2-pyrimidine carboxylic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

A solution of 4,6-bis-(1,1-dimethylethyl)-5-hydroxy-2-pyrimidine carboxylic acid methyl ester (4.0 g, 15.0 mmoles) in 50 mL of THF is added to a suspension of NaH (0.39 g, 16.5 mmoles) in THF (50 mL) at 0° C. When addition is complete, the reaction mixture is stirred at 0° C. for 15 minutes. 2-methoxyethoxymethyl chloride (2.0 g, 16.5 mmoles) is added and the solution is warmed to room temperature. The reaction mixture is stirred at room temperature overnight. It is diluted with 100 mL H2O and 100 mL of saturated aqueous NH4Cl. The layers are separated, and the aqueous phase is washed with Et2O (3×100 mL). The combined organic phases are washed with 100 mL brine and dried over MgSO4. Evaporation of Et2O gives 5.3 g (100%) of the desired ester as an oil.

Provenance & Evidence