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

Participants

Reaction Steps

5-(4-Amino-3-methoxyphenyl)-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (50 mg, 0.147 mmol) was dissolved in dichloromethane (1.5 mL). Pyridine (1.5 mL) was added followed by 1-cyclopentanecarbonyl chloride (31 mg, 0.221 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]-2,2-dimethylpropanamide (33 mg, 0.076 mmol). 1H NMR (CDCl3-d) δ 1.66(m, 2H), 1.81 (m, 2H), 1.95(m, 4H), 2.06(m, 4H), 2.77(m, 1H), 3.65(m, 2H), 3.94(s, 3H), 4.15(m, 2H), 4.96(m, 1H), 5.37(bs, 2H), 6.98(s, 1H), 7.03(s, 1H), 7.07(d, J=8.2 Hz, 1H), 7.84 (s, 1H), 8.30(s, 1H), 8.49(d, J=8.2 Hz, 1H). LC/MS: MH30 =437.

Provenance & Evidence