Dimethylformamide → 4,6-Bis(1,1-dimethylethyl)-5-[(2-methoxyethoxy)-methoxy]-2-pyrimidinecarbonitrile

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Reaction Conditions

Reaction Steps

Dimethylformamide (0.05 g, 0.6 mmoles) is cooled to 0° C. in 10 mL of acetonitrile under argon. Oxalyl chloride (0.1 g, 0.9 mmoles) is added and the reaction mixture is stirred at 0° C. for 10 minutes. 4,6-Bis(1,1-dimethylethyl)-5-[(2-methoxyethoxy)-methoxy] -2-pyrimidinecarboxaldehyde oxime (0.2 g, 0.6 moles) is dissolved in 10 mL of acetonitrile and cooled to 0° C. The vilsmier reagent prepared above is added to the pyrimidine solution at 0° C. After 3 hours at 0° C., the reaction is quenched by the addition of 10 mL of saturated sodium bicarbonate and extracted with ether (3×10 mL). The organic extract is washed with 50 mL of brine and dried over magnesium sulfate. Evaporation of the solvent gives a red oil which is purified by flash chromatography (silica, 10% ether/chloroform) to give 4,6-bis(1,1-dimethylethyl)-5-[(2-methoxyethoxy)-methoxy]-2-pyrimidinecarbonitrile (43 mg, 22% ) as an oil. H1 -NMR (CDCl3) δ 5.04 (s, 2H, O--CH2 --O), 3.95 (m, 2H), 3.62 (m, 2H), 3.41 (s, 3H, OCH3), 1.44 (s, 18H, C(CH3)3 ).

Provenance & Evidence