4-Methoxybenzylamine → 4-Chloro-7-(4-methoxy-benzyl)-5-methyl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine

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Reaction Steps

To a solution of methanesulfonic acid 2-(4,6-dichloro-pyrimidin-5-yl)-propyl ester (0.54 g, 1.89 mmol) in DCM (30 mL) and TEA (4 mL) was added 4-methoxybenzyl amine (0.80 g, 5.83 mmol). The mixture was refluxed overnight. After cooling, the solvent was removed and the residue was subject to column chromatography, eluted by hexane/ethyl acetate (4:1) to give 4-Chloro-7-(4-methoxy-benzyl)-5-methyl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine (0.55 g, 99%). 1H NMR (CDCl3, 400 MHz) δ 8.24 (s, 1H), 7.17 (d, J=7.6 Hz, 2H), 6.86 (d, J=7.6 Hz, 2H), 4.55 (s, 2H), 3.80 (s, 3H), 3.66 (m, 1H), 3.37 (m, 1H), 3.07 (m, 1H), 1.31 (dd, J=7.2 Hz, J=1.2 Hz, 3H). MS (APCI+) [M+H]+291.

Provenance & Evidence