HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → {[3-(3,4-dimethoxybenzyl)-2,4-dioxo-1-(tetrahydro-2H-thiopyran-4-yl)-1,2,3,4-tetrahydroquinazolin-6-yl]oxy}acetonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Bromoacetonitrile | HCID 11534 | — |
| Reactant | 3-(3,4-dimethoxybenzyl)-6-hydroxy-1-(tetrahydro-2H-thiopyran-4-yl)quinazoline-2,4(1H,3H)-dione | HCID 49764281 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | {[3-(3,4-dimethoxybenzyl)-2,4-dioxo-1-(tetrahydro-2H-thiopyran-4-yl)-1,2,3,4-tetrahydroquinazolin-6-yl]oxy}acetonitrile | HCID 46937246 | 0.1% |
Reaction Steps
A mixture of 0.16 g of the compound obtained in Step 3.3, 0.054 g of bromoacetonitrile and 0.243 g of Cs2CO3 in 1 ml of DMF is irradiated in a microwave field for 15 minutes at 100° C. The reaction mixture is evaporated under reduced pressure. The residue is taken up in DCM, washed with water, dried over Na2SO4 and filtered, and the filtrate is evaporated under reduced pressure. The residue is chromatographed on silica gel, eluting with an EtOAc/DCM mixture from (10/90, v/v) to (20/80, v/v) to give 0.138 mg of the expected product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08722659B2 |
| Source dataset | uspto-grants-2014_05 |
| ORD ID | ord-c14433fcdb1f47c98d99788780a1f2b7 |
| Source note | uspto-grants-2014_05 |