p-Fluoronitrobenzene → 3-iodo-1-(4-nitrophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 897763Notes

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.C(=O)([O-])[O-].[Cs+].[Cs+].F[C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=1.C([O-])(=O)C.[NH4+]>CN(C)C=O.O.C(#N)C>[NH2:11][C:9]1[N:8]=[CH:7][N:6]=[C:5]2[N:4]([C:19]3[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=3)[N:3]=[C:2]([I:1])[C:10]=12

Participants

Conditions

Temperature: 80 °C

Procedure

A suspension of 3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (2.00 g, 7.66 mmol) in dimethylformamide (40 mL) was treated with cesium carbonate (3.74 g, 11.49 mmol) and p-fluoronitrobenzene (1.08 g, 7.66 mmol). The reaction mixture stirred at 80° C. for 5 h under a nitrogen atmosphere. The reaction mixture was added to ice. The precipitate was filtered and washed with water. The product, 4-amino-1-[4-nitrophenyl]-3-iodo-1H-pyrazolo[3,4-d]pyrimidine, was dried on the lyophilizer overnight to give 2.55 g (87%). 1H NMR (DMSO-d6, 400 MHz) δ 8.4952-8.4720 (m, 2H), 8.4142-8.3654 (m, 3H); LCMS (Perkin Elmer, Pecosphere C18 column, 3 um particle size, 33×4.6 mm; 100% 50 mM ammonium Acetate in Water to 100% Acetonitrile over 5 min, 3.0 to 3.5 mil/min) tR=3.73 min (100%) M+ 380.6.

Workup

additionThe reaction mixture was added to ice
filtrationThe precipitate was filtered
washwashed with water
dry with materialThe product, 4-amino-1-[4-nitrophenyl]-3-iodo-1H-pyrazolo[3,4-d]pyrimidine, was dried on the lyophilizer overnight
customto give 2.55 g (87%)

Sources & evidence

ORD record: ord-7d232c83f8a94cd9ba3501313457ccda
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06921763B2

Reaction notes

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