Acetic Anhydride → HCID 68603919, compound

HRID 2189164Notes

Reaction equation

[CH2:1]([C:3]1[CH:9]=[C:8]([C:10]2[CH:15]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[O:22][CH2:23][CH2:24][O:25][CH3:26])[NH:13][C:12](=[O:27])[N:11]=2)[CH:7]=[CH:6][C:4]=1[NH2:5])[CH3:2].[C:28]([O:31]C(=O)C)(=O)[CH3:29].C([O-])(=O)C.[K+].[N:40](OCCC(C)C)=O>C(Cl)(Cl)Cl>[CH3:2][C:1]1[C:3]2[C:4](=[CH:6][CH:7]=[C:8]([C:10]3[CH:15]=[C:14]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=4[O:22][CH2:23][CH2:24][O:25][CH3:26])[NH:13][C:12](=[O:27])[N:11]=3)[CH:9]=2)[N:5]([C:28](=[O:31])[CH3:29])[N:40]=1

Participants

Conditions

Temperature: 40 °C

Procedure

A flask was charged with 4-(2-ethylanilin-4-yl)-6-[2-(2-methoxyethoxy)phenyl]-pyrimidin-2(1H)-one (5.5 g, 15 mmol), chloroform (150 mL), acetic anhydride (6.2 mL, 66.7 mmol) and potassium acetate (2.54 g, 30 mmol). The mixture was heated at 40° C. for 2 hours followed by the addition of isoamyl nitrite (5.24 mL, 39 mmol). The resulting mixture was heated to 60° C. overnight, concentrated under reduced pressure, neutralized with sodium bicarbonate, and extracted with EtOAc. The organic layer was concentrated under reduced pressure, and purified by column chromatography to give 4-(3-methyl-1-acetyl-1H-indazol-5-yl)-6-(2-{[2-(methyloxy)ethyl]oxy}phenyl)pyrimidin-2(1H)-one (4.0 g, 65%).

Workup

temperatureThe resulting mixture was heated to 60° C. overnight
concentrationconcentrated under reduced pressure
extractionextracted with EtOAc
concentrationThe organic layer was concentrated under reduced pressure
custompurified by column chromatography

Sources & evidence

ORD record: ord-7a9192bbaa8f4e3f8e1332b02ae6a096
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324231B2

Reaction notes

Loading…