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 2194749Notes

Reaction equation

HRID 2194749 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]-acrylonitrileYield 55%

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, ethyl acetate:hexanes (from 1:1 to 4:1)) to afford 2.7 g (55%) of 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, ethyl acetate:hexanes (from 1:1 to 4:1))

Sources & evidence

ORD record
ord-1e1499d1f1f142a2a1cf4836e5a0a656
Source dataset
uspto-grants-2012_12
Patent number
US08334295B2

Reaction notes

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