HuagongsheHuagongshe Chemistry Print Report · For research reference only
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
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,2,3,4-Tetrahydro-3-methyl-2,4-dioxo5-trimethylsilylethynyl-quinazoline | HCID 14460513 | — |
| Reactant | 6-Ethynyl-4,5-dihydro-4-methyl-3-(5-methyl-1,2,4-oxadiazol-3-yl)-5-oxo-imidazo(1,5-a)quinazoline | HCID 14460522 | — |
| Reactant | HCID 19784294 | HCID 19784294 | — |
| Reactant | 4,5-Dihydro-4-methyl-3-(5-methyl-1,2,4-oxadiazol-3-yl)-5-oxo-6-trimethylsilylethynyl-imidazo(1,5-a)quinazoline | HCID 19865339 | — |
| Product | 4,5-Dihydro-4-methyl-3-(5-methyl-1,2,4-oxadiazol-3-yl)-5-oxo-imidazo(1,5-a)quinazoline | HCID 19865338 | 12% |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04902686 |
| Source dataset | uspto-grants-1990_02 |
| ORD ID | ord-3896b258338c4769989396616a61f3f1 |
| Source note | uspto-grants-1990_02 |