Pyrazole → 7-Methyl-2-pyrazol-1-yl-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one

Participants

Reaction Conditions

Reaction Steps

A high pressure microwave reaction vial was charged with 2-chloro-7-methyl-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one (Intermediate A) (32.7 mg, 178 μmol) and anhydrous tetrahydrofuran (0.5 mL). The reaction was then treated with 1H-pyrazole (22.3 mg, 328 μmol). The vial was tightly sealed and affixed behind a blast shield. The reaction was warmed to 100° C. where it stirred overnight. At this time, the reaction was heated at 100° C. for 30 min in a microwave. The reaction was concentrated in vacuo onto silica gel. Flash chromatography (12 g silica gel column, 1-10% methanol/methylene chloride) afforded 7-methyl-2-pyrazol-1-yl-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one as a white solid (9.6 mg, 25%). 1H NMR (300 MHz, DMSO-d6) δ ppm 3.74 (s, 3H) 6.50 (d, J=3.39 Hz, 1H) 6.67 (dd, J=2.54, 1.79 Hz, 1H) 7.10 (d, J=3.20 Hz, 1H) 7.91 (d, J=1.13 Hz, 1H) 8.61 (d, J=2.45 Hz, 1H) 11.82 (br. s., 1H). LC-MS calcd. for C10H10N5O [(M+H)+] 216, obsd. 215.9.

Provenance & Evidence