Pyridine → N1-[4-(4-amino-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]benzamide

Participants

Reaction Steps

5-(4-Amino-3-methoxyphenyl)-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (80mg, 0.236 mmol) was dissolved in dichloromethane (2.0 mL). Pyridine (2.0 mL) was added followed by 2-pyridinecarbonyl chloride hydrochloride (63 mg, 0.353 mmol). After stirring at room temperature for 2 hours, the solvent was removed and the residue was dissolved in 1 ml DMSO, methanol (1 mL) was added and precipitate was formed. The solid was collected by filtration to give N1-[4-(4-amino-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]benzamide (84 mg, 0.189 mmol). 1H NMR (CDCl3-d) δ 2.12 (m, 4H), 3.67 (m, 2H), 4.03 (s, 3H), 4.14(m, 2H), 5.00 (m, 1H), 5.37 (s, 1H), 7.04(s, 1H), 7.09 (s, 1H), 7.14 (d, J=8.2 Hz, 1H), 7.50 (m, 1H), 7.92 (m, 1H), 8.33 (s, 1H), 8.70(d, J=8.2 Hz, 1H), 10.62 (s, 1H). LC/MS: MH+=445.

Provenance & Evidence