Sodium Cyanide → 6-Cyano-3-(5-cyclopropyl-1,2,4-oxadiazol-3-yl)-4,5-dihydro-4-methyl-5-oxo-imidazo(1,5-a)quinazoline
Reaction equation
Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:24])[N:5]([CH3:23])[C:6]1[N:7]2[CH:12]=[N:13][C:14]=1[C:15]1[N:19]=[C:18]([CH:20]2[CH2:22][CH2:21]2)[O:17][N:16]=1.[C-:25]#[N:26].[Na+]>CN(C)C=O.O>[C:25]([C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:24])[N:5]([CH3:23])[C:6]1[N:7]2[CH:12]=[N:13][C:14]=1[C:15]1[N:19]=[C:18]([CH:20]2[CH2:22][CH2:21]2)[O:17][N:16]=1)#[N:26]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
To 140 mg 6-bromo-3-(5-cyclopropyl-1,2,4-oxadiazol-3-yl)4,5--dihydro-4-methyl-5-oxo-imidazo(1,5-a)quinazoline in 5 ml dimethyl formamide (DMF) 40 mg cuprous cyanide was added. Thereafter further 5 ml DMF was added and the resulting mixture was heated to 130°-150° C. for 60 minutes with stirring. To this mixture 110 mg sodium cyanide in 5 ml water was added and thereafter further 30 ml water. The resulting mixture was extracted with 30 ml ethyl acetate and thereafter four times with 20 ml ethyl acetate. The combined organic phase was washed with water and dried with calcium chloride. Evaporation in vacuo gave 24 mg of the title compound. M.p. 115°-125° C.
Workup
- temperaturethe resulting mixture was heated to 130°-150° C. for 60 minutes
- extractionThe resulting mixture was extracted with 30 ml ethyl acetate
- washThe combined organic phase was washed with water
- dry with materialdried with calcium chloride
- customEvaporation in vacuo
Sources & evidence
- ORD record
- ord-96925f50fd0346b297540a9ed1c16740
- Source dataset
- uspto-grants-1988_10
- Patent number
- US04780539
Reaction notes
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