3-[3-(5-Isopropyl-2,6-dimethoxy-pyrimidine-4-carbonyl)-5-methyl-phenyl]-acrylonitrile → 3-[3-(5-Isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-5-methyl-phenyl]-acrylonitrile

HRID 426183Notes

Reaction equation

HRID 426183 reaction equation
[CH:1]([C:4]1[C:5]([C:14]([C:16]2[CH:17]=[C:18]([CH:23]=[CH:24][C:25]#[N:26])[CH:19]=[C:20]([CH3:22])[CH:21]=2)=[O:15])=[N:6][C:7]([O:12]C)=[N:8][C:9]=1[O:10]C)([CH3:3])[CH3:2]>C1COCC1.C(Cl)(=O)C(Cl)=O>[CH:1]([C:4]1[C:9](=[O:10])[NH:8][C:7](=[O:12])[NH:6][C:5]=1[C:14]([C:16]1[CH:17]=[C:18]([CH:23]=[CH:24][C:25]#[N:26])[CH:19]=[C:20]([CH3:22])[CH:21]=1)=[O:15])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 667055443-[3-(5-Isopropyl-2,6-dimethoxy-pyrimidine-4-carbonyl)-5-methyl-phenyl]-acrylonitrile

Product 1

HCID 667053903-[3-(5-Isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-5-methyl-phenyl]-acrylonitrile

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 65578Oxalyl chlorideSolvent

Procedure

To a stirred solution of 3-[3-(5-isopropyl-2,6-dimethoxy-pyrimidine-4-carbonyl)-5-methyl-phenyl]-acrylonitrile (5.36 g, 15.27 mmol) in anhydrous THF (50 ml), oxalyl chloride (25 ml) was added. The mixture was then refluxed with vigorous stirring for overnight. After cooling to room temperature, the mixture was evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, EA: hexanes (from 1:1 to 4:1)) to afford 2.7 g (55%) of the a white solid. m.p. 233-235° C.; 1H NMR (300 MHz, CD3OD/CDCl3) δ 1.16 (6H, d, J=6.9 Hz), 2.39-2.56 (4H, m), 6.12 (1H, d, J=16.6 Hz), 7.49 (1H, d, J=16.6 Hz), 7.66 (1H, s), 7.83 (1H, s), 7.87 (1H, s); m/z (LC/Mass, EI) 324 (M+H+).

Workup

  1. temperatureThe mixture was then refluxed
  2. customthe mixture was evaporated in vacuo
  3. customthe residue was purified by silica gel column chromatography (eluent, EA: hexanes (from 1:1 to 4:1))
  4. customto afford 2.7 g (55%) of the a white solid

Sources & evidence

ORD record
ord-1695fba4c0954b6a9dd802d152400050
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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