Acetic Anhydride → 6-(5-Methyl-1,3,4-oxadiazol-2-yl)-pyrido[3,4-d]pyrimidin-4-one

Reaction equation

N1[C:5]([C:6]2[N:16]=[CH:15][C:9]3[N:10]=[CH:11][NH:12][C:13](=[O:14])[C:8]=3[CH:7]=2)=[N:4][N:3]=N1.[C:17](OC(=O)C)(=[O:19])[CH3:18]>>[CH3:18][C:17]1[O:19][C:5]([C:6]2[N:16]=[CH:15][C:9]3[N:10]=[CH:11][NH:12][C:13](=[O:14])[C:8]=3[CH:7]=2)=[N:4][N:3]=1

Participants

Reactant 2

HCID 7918Acetic Anhydride

HCID 178518713HCID 178518713, compound

Product 1

HCID 1358174476-(5-Methyl-1,3,4-oxadiazol-2-yl)-pyrido[3,4-d]pyrimidin-4-one

Procedure

6-(1,2,3,4-Tetrazol-5-yl)-pyrido[3,4-d]pyrimidin-4-one (1.4 g) in acetic anhydride (10 ml) was heated at reflux under N2 for 2.5 hours. The cooled mixture was absorbed onto silica and purified by chromatography to give the title compound 90.14 g) as a beige solid; δH [2H6]DMSO 13.0(1H,bs), 9.30 (1H,s), 8.66 (1H,s), 8.47 (1H,s) 2.75 (3H,s); m/z (M+1+)230.

Workup

temperatureat reflux under N2 for 2.5 hours
customThe cooled mixture was absorbed onto silica
custompurified by chromatography

Sources & evidence

ORD record: ord-559d1d2348d94bf3a8cbb08d9107386b
Source dataset: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06174889B1

Reaction notes

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