Potassium Carbonate → 3-((4-Amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)-4-phenyl-1H-isochromen-1-one

HRID 634405Notes

Reaction equation

[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[NH2:11])[NH:4][N:3]=1.Br[CH2:13][C:14]1[O:15][C:16](=[O:30])[C:17]2[C:22]([C:23]=1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[CH:21][CH:20]=[CH:19][CH:18]=2.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[NH2:11][C:9]1[N:8]=[CH:7][N:6]=[C:5]2[N:4]([CH2:13][C:14]3[O:15][C:16](=[O:30])[C:17]4[C:22]([C:23]=3[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)=[CH:21][CH:20]=[CH:19][CH:18]=4)[N:3]=[C:2]([I:1])[C:10]=12

Participants

Conditions

Temperature: 50 °C

Procedure

Commercially available 3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (124 mg, 0.476 mmol) was added to a solution of 3-(bromomethyl)-4-phenyl-1H-isochromen-1-one (intermediate C1, 100 mg, 0.317 mmol) in DMF (1 mL). K2CO3 (65.8 mg, 0.476 mmol) was added and the resulting mixture was stirred at 50° C. for 2 hrs. The resulting crude was straightforward purified via reverse phase chromatography with a Biotage C18 SNAP 30 g column (Phase A, water 95%, ACN 5%, formic acid 0.01%); Phase B ACN 95%, water 5%, formic acid 0.01%) to give the title compound (138 mg, 88%).

Workup

customThe resulting crude was straightforward purified via reverse phase chromatography with a Biotage C18 SNAP 30 g column (Phase A, water 95%, ACN 5%, formic acid 0.01%)

Sources & evidence

ORD record: ord-f091ed3cc1524ccb8ef96d48bde24147
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321776B2

Reaction notes

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