Dimethyl Sulfoxide → HCID 118023631, compound

HRID 2171797Notes

Reaction equation

HRID 2171797 reaction equation
Cl[C:2]1[C:3]2[CH:11]=[C:10]([CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]3)[S:9][C:4]=2[N:5]=[C:6]([CH3:8])[N:7]=1.C1N2CC[N:20](CC2)[CH2:19]1.CS(C)=O.[C-]#N.[K+]>O>[CH:12]1([C:10]2[S:9][C:4]3[N:5]=[C:6]([CH3:8])[N:7]=[C:2]([C:19]#[N:20])[C:3]=3[CH:11]=2)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 9032Potassium CyanideHCID 9237DabcoHCID 118023129HCID 118023129, compound

Product 1

HCID 118023631HCID 118023631, compoundYield 860.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 4-chloro-6-cyclohexyl-2-methylthieno[2,3-d]pyrimidine (27.3 g), DABCO (1.2 g) and DMSO (150 mL) was slowly added an aqueous solution (14 mL) of KCN (8 g), followed by stirring at room temperature for 15 hours. To the reaction mixture was added water (150 mL) under ice-cooling, followed by stirring. The precipitate was collected by filtration and dissolved in chloroform. To the organic layer were added MgSO4, activated carbon (2 g), and basic silica gel (100 mL), followed by stirring. The mixture was filtered through Celite and then concentrated under reduced pressure to obtain 6-cyclohexyl-2-methylthieno[2,3-d]pyrimidine-4-carbonitrile (23.7 g).

Workup

  1. temperaturecooling
  2. stirringby stirring
  3. filtrationThe precipitate was collected by filtration
  4. dissolutiondissolved in chloroform
  5. additionTo the organic layer were added MgSO4, activated carbon (2 g), and basic silica gel (100 mL)
  6. stirringby stirring
  7. filtrationThe mixture was filtered through Celite
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bcf96842ec4c4e28959e26997ee08a19
Source dataset
uspto-grants-2015_06
Patent number
US09051339B2

Reaction notes

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