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

HRID 2226426Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[N:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:8]([OH:15])=[C:7]([C:16]([CH3:19])([CH3:18])[CH3:17])[N:6]=1)=[O:4].[H-].[Na+].[CH3:22][O:23][CH2:24][CH2:25][O:26][CH2:27]Cl>C1COCC1.O.[NH4+].[Cl-]>[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([C:16]([CH3:19])([CH3:18])[CH3:17])[C:8]([O:15][CH2:22][O:23][CH2:24][CH2:25][O:26][CH3:27])=[C:9]([C:11]([CH3:12])([CH3:13])[CH3:14])[N:10]=1)=[O:4]

Participants

Conditions

Temperature: 0 °C

Procedure

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.

Workup

additionWhen addition
temperaturethe solution is warmed to room temperature
stirringThe reaction mixture is stirred at room temperature overnight
customThe layers are separated
washthe aqueous phase is washed with Et2O (3×100 mL)
washThe combined organic phases are washed with 100 mL brine
dry with materialdried over MgSO4
customEvaporation of Et2O

Sources & evidence

ORD record: ord-7303130ac0bd43f19cb4a43613937111
Source dataset: uspto-grants-1994_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05348957

Reaction notes

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