Potassium Cyanide → 7H-Pyrrolo[2,3-d]pyrimidine-4-carbonitrile

HRID 888129Notes

Reaction equation

HRID 888129 reaction equation
Cl[C:2]1[C:3]2[CH:10]=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.C1(C)C=CC(S(O)=O)=CC=1.[Na].[C-:22]#[N:23].[K+]>CS(C)=O.O>[N:5]1[C:4]2[NH:8][CH:9]=[CH:10][C:3]=2[C:2]([C:22]#[N:23])=[N:7][CH:6]=1

Participants

7

Reactant 4

HCID 9032Potassium CyanideHCID 10818p-Toluenesulfinic acidHCID 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-HCID 5360545Sodium

Product 1

HCID 552884807H-Pyrrolo[2,3-d]pyrimidine-4-carbonitrile

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Commercially available 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (1 g, 6.51 mmol) was dissolved in DMSO (15 mL) then p-toluenesulfinic acid, sodium salt (1.16 g, 6.51 mmol) and KCN (635 mg, 9.76 mmol) were added. The reaction mixture was heated at 100° C. for 17 h, cooled to RT and diluted with water. The mixture was extracted with EtOAc. The organic layers were washed with brine, dried over MgSO4 and concentrated in vacuo to give 7H-pyrrolo[2,3-d]pyrimidine-4-carbonitrile as a light yellow solid.

Workup

  1. temperaturecooled to RT
  2. extractionThe mixture was extracted with EtOAc
  3. washThe organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-833c1ae2d1d14930b150fb7ee3264b27
Source dataset
uspto-grants-2012_08
Patent number
US08247556B2

Reaction notes

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