Potassium Cyanide → HCID 69793868, compound

HRID 1278917Notes

Reaction equation

HRID 1278917 reaction equation
[C:1]([N:8]1[CH:13]=[C:12]([CH2:14][NH2:15])[CH:11]=[N:10][CH:9]1S(C)(=O)=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C-:20]#[N:21].[K+].C1OCCOCCOCCOCCOCCOC1>CN(C=O)C>[C:1]([N:8]1[CH:13]=[C:12]([CH2:14][NH2:15])[CH:11]=[N:10][CH:9]1[C:20]#[N:21])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 9032Potassium CyanideHCID 2855718-Crown-6HCID 69797027HCID 69797027, compound

Product 1

HCID 69793868HCID 69793868, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

1 Eq. of N-Boc-5-aminomethyl-2-methylsulfonylpyrimidine was dissolved in DMF and introduced into a reflux apparatus. After addition of 2 eq. of KCN and catalytic amounts of 18-crown-6, the reaction mixture was stirred at 60° C. for 4 h. The suspension was then concentrated and poured into 200 ml of water. The precipitated solid was filtered off with suction and dissolved in ethyl acetate. The solution was washed with water and saturated NaCl solution, dried and evaporated in a rotary evaporator. N-Boc-5-aminomethyl-2-cyanopyrimidine was used as crude product without further purification in the next reaction. Yield: 46%.

Workup

  1. additionintroduced into a reflux apparatus
  2. concentrationThe suspension was then concentrated
  3. additionpoured into 200 ml of water
  4. filtrationThe precipitated solid was filtered off with suction
  5. dissolutiondissolved in ethyl acetate
  6. washThe solution was washed with water and saturated NaCl solution
  7. customdried
  8. customevaporated in a rotary evaporator
  9. customN-Boc-5-aminomethyl-2-cyanopyrimidine was used as crude product without further purification in the next reaction

Sources & evidence

ORD record
ord-2a89cbb415a54bf586dffc0c34fb5893
Source dataset
uspto-grants-2002_09
Patent number
US06444817B1

Reaction notes

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