Acetic Anhydride → HCID 66672882, compound

HRID 422047Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[O:20][CH2:21][CH2:22][CH3:23])[NH:11][C:10](=[O:24])[N:9]=2)=[CH:4][C:3]=1[CH3:25].[C:26]([O-:29])(=O)[CH3:27].[Na+].[C:31]([O:34]C(=O)C)(=O)[CH3:32].[N:38](OCCC(C)C)=O>C(Cl)(Cl)Cl>[C:31]([N:11]1[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH2:21][CH2:22][CH3:23])=[CH:13][C:8]([C:5]2[CH:4]=[C:3]3[C:2](=[CH:7][CH:6]=2)[N:1]([C:26](=[O:29])[CH3:27])[N:38]=[CH:25]3)=[N:9][C:10]1=[O:24])(=[O:34])[CH3:32]

Participants

Conditions

Temperature: 75 °C

Procedure

To a stirred solution of 4-(4-amino-3-methylphenyl)-6-[2-(propyloxy)phenyl]pyrimidin-2(1H)-one (2.10 g, 6.27 mmol) and sodium acetate (3.10 g, 31.3 mmol) in chloroform (80 mL) at room temperature was added acetic anhydride (3.0 mL, 31.3 mmol) and stirred for 15 min. The reaction mixture was warmed to 75° C. and added drop-wise isoamyl nitrite (5.10 g, 38 mmol) then stirred at 65° C. for 18 h. The reaction mixture was cooled to room temperature and washed with water (100 mL) and saturated aqueous sodium bicarbonate (100 mL). The solution was dried over anhydrous sodium sulfate, concentrated in vacuo, and purified by flash chromatography (SiO2, ethyl acetate/hexanes 1:2) to afford 1-acetyl-4-(1-acetyl-1H-indazol-5-yl)-6-[2-(propyloxy)phenyl]pyrimidin-2(1H)-one (1.06 g, 40%). MS (EI) for C24H22N4O4: 431 (MH+).

Workup

stirringthen stirred at 65° C. for 18 h
temperatureThe reaction mixture was cooled to room temperature
washwashed with water (100 mL) and saturated aqueous sodium bicarbonate (100 mL)
dry with materialThe solution was dried over anhydrous sodium sulfate
concentrationconcentrated in vacuo
custompurified by flash chromatography (SiO2, ethyl acetate/hexanes 1:2)

Sources & evidence

ORD record: ord-6353bd72622f4b6cb3c9e4a3c3876082
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08101625B2

Reaction notes

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