Potassium Cyanide → 6-(4,4-Dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidine-4-carbonitrile
Reaction equation
Cl[C:2]1[C:3]2[CH:11]=[C:10]([CH:12]3[CH2:17][CH2:16][C:15]([CH3:19])([CH3:18])[CH2:14][CH2:13]3)[S:9][C:4]=2[N:5]=[C:6]([CH3:8])[N:7]=1.CS(O[Na])=O.[C-:25]#[N:26].[K+]>CN(C=O)C>[CH3:18][C:15]1([CH3:19])[CH2:16][CH2:17][CH:12]([C:10]2[S:9][C:4]3[N:5]=[C:6]([CH3:8])[N:7]=[C:2]([C:25]#[N:26])[C:3]=3[CH:11]=2)[CH2:13][CH2:14]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
To a mixture of 4-chloro-6-(4,4-dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidine (31.1 g) and DMF (220 mL) were added CH3SO2Na (11 g) and KCN (10 g), followed by heating and stirring at 70° C. for 15 hours. The reaction mixture was concentrated to about a half of the amount under reduced pressure, diluted with water (300 mL), and then stirred. The precipitate was collected by filtration. To the precipitate was added chloroform, followed by dissolving therein, and MgSO4, activated carbon (10 g), and silica gel (100 mL) were added thereto, followed by stirring. The mixture was filtered through Celite and then concentrated under reduced pressure to obtain 6-(4,4-dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidine-4-carbonitrile (27.4 g).
Workup
- temperatureby heating
- concentrationThe reaction mixture was concentrated to about a half of the amount under reduced pressure
- additiondiluted with water (300 mL)
- stirringstirred
- filtrationThe precipitate was collected by filtration
- additionTo the precipitate was added chloroform
- dissolutionby dissolving
- additionMgSO4, activated carbon (10 g), and silica gel (100 mL) were added
- stirringby stirring
- filtrationThe mixture was filtered through Celite
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-919d24e337be4d378482a6cbc3db36a6
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09051339B2
Reaction notes
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