1,2,3,4-Tetrahydro-3-methyl-2,4-dioxo5-trimethylsilylethynyl-quinazoline → 4,5-Dihydro-4-methyl-3-(5-methyl-1,2,4-oxadiazol-3-yl)-5-oxo-imidazo(1,5-a)quinazoline

HRID 2351315Notes

Reaction equation

HRID 2351315 reaction equation
C([C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5](=[O:23])[N:6]([CH3:22])[C:7]1[N:8]2[CH:13]=[N:14][C:15]=1[C:16]1[N:20]=[C:19]([CH3:21])[O:18][N:17]=1)#C.CC1ON=C(C[N+]#[C-])N=1.CN1C(=O)C2C(=CC=CC=2C#C[Si](C)(C)C)NC1=O>>[CH3:22][N:6]1[C:5](=[O:23])[C:4]2[C:9](=[CH:10][CH:11]=[CH:12][CH:3]=2)[N:8]2[CH:13]=[N:14][C:15]([C:16]3[N:20]=[C:19]([CH3:21])[O:18][N:17]=3)=[C:7]12

Participants

4

Reactant 3

HCID 144605131,2,3,4-Tetrahydro-3-methyl-2,4-dioxo5-trimethylsilylethynyl-quinazolineHCID 144605226-Ethynyl-4,5-dihydro-4-methyl-3-(5-methyl-1,2,4-oxadiazol-3-yl)-5-oxo-imidazo(1,5-a)quinazoline2×HCID 19784294HCID 19784294, compound

Product 1

HCID 198653384,5-Dihydro-4-methyl-3-(5-methyl-1,2,4-oxadiazol-3-yl)-5-oxo-imidazo(1,5-a)quinazolineYield 12%

Procedure

6-ethynyl-4,5-dihydro-4-methyl-3-(5-methyl-1,2,4-oxadiazol-3-yl)-5-oxo-imidazo(1,5-a)quinazoline, M.p. 202-206° C.. by reaction between 5-methyl-3-isocyanomethyl-1,2,4-oxadiazole and 1,2,3,4-tetrahydro-3-methyl-2,4-dioxo-5-trimethylsilylethynyl-quinazoline. Column chromatography(silica gel)ethyl acetate) of the crude product yielded 0.08g (12%) of 4,5-dihydro-4-methyl-3-(5-methyl-1,2,4-oxadiazol-3-yl)-5-oxo-imidazo(1,5-a)quinazoline and 0.Olg (1.9%) of 6-ethynyl-4,5-dihydro-4-methyl-3-(5-methyl-1,2,4-oxadiazol-3-yl)-5-oxo-imidazo(1,5-a)quinazoline.

Sources & evidence

ORD record
ord-adbd4a95f1f5434b86234de87a11d896
Source dataset
uspto-grants-1989_10
Patent number
US04873244

Reaction notes

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