Pyridine → N5-[4-(4-amino-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]-1,3-dimethyl-1H-5-pyrazolecarboxamide

Participants

Reaction Steps

5-(4-Amino-3-methoxyphenyl)-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (80 mg, 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 I ml DMSO, methanol (1 mL) was added and precipitate was formed. The solid was collected by filtration to give N5-[4-(4-amino-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]-1,3-dimethyl-1H-5-pyrazolecarboxamide (30 mg, 0.065 mmol). 1H NMR (CDCl3-d) δ 2.11 (m, 4H), 2.32(s, 3H), 3.66(m, 2H), 3.99(s, 3H), 4.13(m, 2H), 4.17(s, 3H), 4.99(m, 1H), 5.22(bs, 2H), 6.46(s, 1H), 7.03 (s, 1H), 7.07(s, 1H), 7.12(d, J=8.2 Hz, 1H), 8.33 (2, 2H), 8.49(d, J=8.2 Hz, 1H). LC/MS: MH+=462.

Provenance & Evidence