4-Methoxybenzylamine → 3-{3-[6-Chloro-2-(4-methoxy-benzylamino)-pyrimidin-4-ylmethyl]-5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl}-5-methyl-benzonitrile

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Reaction Steps

A mixture of 3-[3-(2,6-Dichloro-pyrimidin-4-ylmethyl)-5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl]-5-methyl-benzonitrile (458 mg, 1 mmol) and p-methoxy benzylamine (262 μl, 2 mmol) in acetonitrile (10 ml) was refluxed for 2.5 hr. After cooling to room temperature, the mixture was evaporated in vacuo. The residue was dissolved in dichloromethane (20 ml), washed with water, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo. The residue was purified by silica gel column chromatography (eluent, EA:hexane (1:2)) to afford 143 mg (25%) of 3-{3-[2-Chloro-6-(4-methoxy-benzylamino)-pyrimidin-4-ylmethyl]-5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl}-5-methyl-benzonitrile (Rf=0.14) and 302 mg (54%) of 3-{3-[6-Chloro-2-(4-methoxy-benzylamino)-pyrimidin-4-ylmethyl]-5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl}-5-methyl-benzonitrile (Rf=0.06) as a white solid, respectively.

Provenance & Evidence