phenyl N-[4-(4-amino-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]carbamate → (4-bromo-1,3-thiazol-5-yl)methyl N-[4-(4-amino-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]carbamate

Participants

Reaction Conditions

Reaction Steps

Phenyl N-[4-(4-amino-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]carbamate (28 mg, 0.061 mmol) was mixed with (4-bromo-1,3-thiazol-5-yl)methanol (50 mg, 0.434 mmol) in pyridine (0.5 mL). The reaction mixture was heated at 100° C. overnight. The solvent was removed and the residue was purified by preparative reverse phase LC/MS to give (4-bromo-1,3-thiazol-5-yl)methyl N-[4-(4-amino-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]carbamate. 1H NMR (CDCl-d) δ 2.07(m, 4H), 3.65(m, 2H), 3.92(s, 3H), 4.13(m, 2H), 4.98(m, 1H), 5.35(s, 1H), 5.40(s, 2H), 6.97(s, 1H), 7.04(s, 1H), 7.09(m, 1H), 7.35(s, 1H), 8.17(s, 1H), 8.32(s, 1H), 8.78(s, 1H). LC/MS MH+=481.

Provenance & Evidence