Ammonia → 7-methoxy-2-(4-methoxyphenyl)-5H-pyrimido[5,4-b]indole-4-carboxamide

HRID 2410737Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:7]3[N:15]=[C:14]([C:16]4[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=4)[N:13]=[C:12]([C:24]([O:26]C)=O)[C:8]=3[NH:9][C:10]=2[CH:11]=1.[NH3:28]>CO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:7]3[N:15]=[C:14]([C:16]4[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=4)[N:13]=[C:12]([C:24]([NH2:28])=[O:26])[C:8]=3[NH:9][C:10]=2[CH:11]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A suspension of methyl 7-methoxy-2-(4-methoxyphenyl)-5H-pyrimido[5,4-b]indole-4-carboxylate (97 mg, 0.27 mmol) in a 7 N solution of ammonia in MeOH (10 mL) in a sealed microwave vial was heated at 80° C. overnight. The solvent was removed and the residue was suspended in EtOAc. Filtration gave 7-methoxy-2-(4-methoxyphenyl)-5H-pyrimido[5,4-b]indole-4-carboxamide (58 mg) as a yellow solid. MS (ESI) m/z 349.0 (M+H). 1H NMR (DMSO-d6) δ ppm 11.68 (1H, br. s.), 8.59-8.73 (3H, m), 8.20 (1H, d, J=8.85 Hz), 8.05 (1H, s), 7.29 (1H, d, J=2.14 Hz), 7.08 (2H, d, J=8.85 Hz), 6.96 (1H, dd, J=8.70, 2.29 Hz), 3.90 (3H, s), 3.87 (3H, s).

Workup

customThe solvent was removed
filtrationFiltration

Sources & evidence

ORD record: ord-06f22d94c4ba4a00956f7b210413e373
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815840B2

Reaction notes

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