Sodium hydride → 3-Iodo-1-(3-methoxy-4-nitrophenyl)-1H-pyrazolo[4,3-d]pyrimidin-7-amine

HRID 1171023Notes

Reaction equation

[I:1][C:2]1[C:6]2[N:7]=[CH:8][N:9]=[C:10]([NH2:11])[C:5]=2[NH:4][N:3]=1.F[C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[C:15]([O:22][CH3:23])[CH:14]=1.[H-].[Na+]>CN(C)C=O>[I:1][C:2]1[C:6]2[N:7]=[CH:8][N:9]=[C:10]([NH2:11])[C:5]=2[N:4]([C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[C:15]([O:22][CH3:23])[CH:14]=2)[N:3]=1

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of 3-iodo-1H-pyrazolo[4,3-d]pyrimidin-7-amine (500 mg, 1.92 mmol) and 4-fluoro-2-methoxy-1-nitrobenzene (360 mg, 2.11 mmol) in N,N-dimethylformamide (5 mL) was treated with 60% sodium hydride in oil (92 mg, 2.30 mmol) then heated in an 85° C. oil bath for 17 hours. The solvent was removed by evaporation under reduced pressure then the residue was dissolved in a minimum of hot N,N-dimethylformamide and applied to a silica gel column and eluted with ethyl acetate to provide the title compound (405 mg, 51%) as a yellow solid after concentration of the appropriate fractions: 1H NMR (DMSO-d6, 400 MHz) δ 8.38 (s, 1H), 8.10 (d, 1H), 7.47 (s, 1H), 7.30 (m, 1H), 7.15 (bs, 2H), 3.98 (s, 3H); RP-HPLC (Hypersil HS C18, 5 μm, 100 A, 250×4.6 mm; 5%-100% acetonitrile-0.05 M ammonium acetate over 25 min, 1 mL/min) tr 16.17 min; MS: MH+ 413.1, M−H+ 411.1

Workup

customThe solvent was removed by evaporation under reduced pressure
dissolutionthe residue was dissolved in a minimum of hot N,N-dimethylformamide
washeluted with ethyl acetate

Sources & evidence

ORD record: ord-3f37213f42cb4af7b16ae0dce9881c4b
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07829570B2

Reaction notes

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