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 1199653Notes

Reaction equation

HRID 1199653 reaction equation
[CH3:1][N:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2C#C[Si](C)(C)C)[N:4]2[CH:19]=[N:20][C:21]([C:22]3[N:26]=[C:25]([CH3:27])[O:24][N:23]=3)=[C:3]12.C(C1C=CC=C2C=1C(=O)N(C)C1N2C=NC=1C1N=C(C)ON=1)#C.CC1ON=C(C[N+]#[C-])N=1.CN1C(=O)C2C(=CC=CC=2C#C[Si](C)(C)C)NC1=O>>[CH3:1][N:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]2[CH:19]=[N:20][C:21]([C:22]3[N:26]=[C:25]([CH3:27])[O:24][N:23]=3)=[C:3]12

Participants

5

Reactant 4

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)quinazolineHCID 19784294HCID 19784294, compoundHCID 198653394,5-Dihydro-4-methyl-3-(5-methyl-1,2,4-oxadiazol-3-yl)-5-oxo-6-trimethylsilylethynyl-imidazo(1,5-a)quinazoline

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

A mixture of 4,5-Dihydro-4-methyl-3-(5-methyl-1,2,4-oxadiazol-3-yl)-5-oxo-6-trimethylsilylethynyl-imidazo(1,5-a)quinazoline, M.p. 214°-217° C., and 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 0.08 g (12%) of 4,5-dihydro-4-methyl-3-(5-methyl-1,2,4-oxadiazol-3-yl)-5-oxo-imidazo(1,5-a)quinazoline and 0.01 g (1.9%) of 6-ethylnyl-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-3896b258338c4769989396616a61f3f1
Source dataset
uspto-grants-1990_02
Patent number
US04902686

Reaction notes

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