Dimethylformamide → 1-benzyl-3-(1-cyanocycloprop-1-ylmethyl)-5-methyl-2,4(1H,3H)-pyrimidinedione

HRID 342557Notes

Reaction equation

HRID 342557 reaction equation
CS(O[CH2:6][C:7]1([C:10]#[N:11])[CH2:9][CH2:8]1)(=O)=O.CN(C=O)C.[CH2:17]([N:24]1[CH:29]=[C:28]([CH3:30])[C:27](=[O:31])[NH:26][C:25]1=[O:32])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[H-].[Na+]>O.[Cl-].[NH4+]>[CH2:17]([N:24]1[CH:29]=[C:28]([CH3:30])[C:27](=[O:31])[N:26]([CH2:6][C:7]2([C:10]#[N:11])[CH2:9][CH2:8]2)[C:25]1=[O:32])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

7

Reactant 4

HCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 2379531-Benzyl-5-methyl-1H-pyrimidine-2,4-dioneHCID 54220629(1-Cyanocyclopropyl)methyl methanesulfonate

Product 1

HCID 702014981-benzyl-3-(1-cyanocycloprop-1-ylmethyl)-5-methyl-2,4(1H,3H)-pyrimidinedione

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 25517Ammonium ChlorideSolvent

Procedure

A mixture of the 1-cyanocycloprop-1-ylmethyl methanesulfonate and DMF (78 mL) was added to a mixture of 1-benzyl-5-methyl-2,4(1H,3H)-pyrimidinedione (9.1 g, 42.2 mmol), 60% sodium hydride (1.95 g, 48.8 mmol) and DMF (117 mL) at 0° to 5° C. The mixture was heated 20 hours at 45° to 55° C., then diluted with water (20 mL) and saturated ammonium chloride (20 mL) and extracted with ethyl acetate. The extract was washed with water and then brine, dried (MgSO4) and concentrated to dryness. The residue was purified by flash chromatography on silica gel eluting with hexane/ethyl acetate (1:1) to give 1-benzyl-3-(1-cyanocycloprop-1-ylmethyl)-5-methyl-2,4(1H,3H)-pyrimidinedione (10.4 g, 35.2 mmol).

Workup

  1. temperatureThe mixture was heated 20 hours at 45° to 55° C.
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialbrine, dried (MgSO4)
  5. concentrationconcentrated to dryness
  6. customThe residue was purified by flash chromatography on silica gel eluting with hexane/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-612fa9be0b29442c9426a5da650b12ad
Source dataset
uspto-grants-1999_01
Patent number
US05859014

Reaction notes

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