Chloroacetonitrile → 6-Chloro-1-cyanomethyl-3-propylpyrimidine-2,4(1H,3H)-dione

HRID 1090637Notes

Reaction equation

HRID 1090637 reaction equation
Cl[CH2:2][C:3]#[N:4].C(=O)([O-])[O-].[K+].[K+].[Cl:11][C:12]1[NH:17][C:16](=[O:18])[N:15]([CH2:19][CH2:20][CH3:21])[C:14](=[O:22])[CH:13]=1>CN(C=O)C.C(Cl)(Cl)Cl>[Cl:11][C:12]1[N:17]([CH2:2][C:3]#[N:4])[C:16](=[O:18])[N:15]([CH2:19][CH2:20][CH3:21])[C:14](=[O:22])[CH:13]=1

Participants

6

Reactant 3

HCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 6408466-chloro-3-propylpyrimidine-2,4(1H,3H)-dione

Product 1

HCID 150275436-Chloro-1-cyanomethyl-3-propylpyrimidine-2,4(1H,3H)-dione

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

Chloroactonitrile (16.5 g) and potassium carbonate (29.3 g) were added to a solution of 6-chloro-3-propylpyrimidine-2,4(1H,3H)-dione (20 g) in DMF (200 ml), and the mixture was stirred at room temperature for 24 hours. The reaction solution was concentrated and evaporated to dryness to obtain a residue. A resulting residue was dissolved in chloroform and H2O, and the organic layer was washed with water and dried. The solvent was evaporated to dryness to give a syrup, which was purified by column chromatography on silica gel to give a crystalline product. Recrystalization of the crude crystals from ethyl acetate-isopropylether gave colorless prisims (21.1 g, 87%), mp. 83°-84° C.

Workup

  1. concentrationThe reaction solution was concentrated
  2. customevaporated to dryness
  3. customto obtain a residue
  4. washH2O, and the organic layer was washed with water
  5. customdried
  6. customThe solvent was evaporated to dryness
  7. customto give a syrup, which
  8. customwas purified by column chromatography on silica gel
  9. customto give a crystalline product
  10. customRecrystalization of the crude crystals from ethyl acetate-isopropylether
  11. customgave colorless prisims (21.1 g, 87%), mp. 83°-84° C.

Sources & evidence

ORD record
ord-4691d2f1ddb6403da9240234b5a40fd9
Source dataset
uspto-grants-1992_01
Patent number
US05082838

Reaction notes

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