3-(4-methoxybenzyl)pyrazolo[3,4-b]pyrrolo[3,4-d]pyridine-6,8(3H,7H)-dione → pyrazolo[3,4-b]pyrrolo[3,4-d]pyridine-6,8(3H,7H)-dione

HRID 1400107Notes

Reaction equation

COC1C=CC(C[N:8]2[C:12]3=[N:13][CH:14]=[C:15]4[C:19](=[O:20])[NH:18][C:17](=[O:21])[C:16]4=[C:11]3[CH:10]=[N:9]2)=CC=1>FC(F)(F)C(O)=O>[CH:10]1[C:11]2[C:12](=[N:13][CH:14]=[C:15]3[C:19](=[O:20])[NH:18][C:17](=[O:21])[C:16]3=2)[NH:8][N:9]=1

Participants

Conditions

Temperature: 65 °C

Procedure

3-(4-methoxybenzyl)pyrazolo[3,4-b]pyrrolo[3,4-d]pyridine-6,8(3H,7H)-dione (100 mg, 0.32 mmol) was dissolved in trifluoroacetic acid (5 ml) and heated to 65° C. for 24 hours. The mixture was concentrated under reduced pressure and partitioned between ethyl acetate (100 ml) and saturated aqueous sodium bicarbonate (50 ml). The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was treated with ethyl acetate (3 ml) and a few drops of methanol and cooled to 0° C. The mixture was filtered and washed with ice cold ethyl acetate to afford pyrazolo[3,4-b]pyrrolo[3,4-d]pyridine-6,8(3H,7H)-dione (28 mg, 47%) as a yellow solid. M.p.=285-300° C.; 400 MHz 1H NMR (DMSO-d6) δ: 11.55 (bs, 1H), 8.98 (s, 1H), 8.50 (s, 1H); LCMS: 189 [M+H].

Workup

concentrationThe mixture was concentrated under reduced pressure
custompartitioned between ethyl acetate (100 ml) and saturated aqueous sodium bicarbonate (50 ml)
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
additionThe crude product was treated with ethyl acetate (3 ml) and a few drops of methanol
temperaturecooled to 0° C
filtrationThe mixture was filtered
washwashed with ice cold ethyl acetate

Sources & evidence

ORD record: ord-32fd23203e3f415fae5fbcb6a552eb2b
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08906928B2

Reaction notes

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