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

HRID 1022446Notes

Reaction equation

Cl[C:2]1[NH:3][C:4](=[O:12])[C:5]2[CH:10]=[CH:9][N:8]([CH3:11])[C:6]=2[N:7]=1.[NH:13]1[CH:17]=[CH:16][CH:15]=[N:14]1>O1CCCC1>[CH3:11][N:8]1[C:6]2[N:7]=[C:2]([N:13]3[CH:17]=[CH:16][CH:15]=[N:14]3)[NH:3][C:4](=[O:12])[C:5]=2[CH:10]=[CH:9]1

Participants

Conditions

Temperature: 100 °C

Procedure

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.

Workup

customA high pressure microwave reaction
customThe vial was tightly sealed
temperatureAt this time, the reaction was heated at 100° C. for 30 min in a microwave
concentrationThe reaction was concentrated in vacuo onto silica gel

Sources & evidence

ORD record: ord-ba55d50cef9a41cf9343c3b96943d039
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722661B2

Reaction notes

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