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

HRID 426188Notes

Reaction equation

HRID 426188 reaction equation
[CH2:1]([C:3]1[C:4]([C:13]([C:15]2[CH:16]=[C:17]([CH:22]=[CH:23][C:24]#[N:25])[CH:18]=[C:19]([CH3:21])[CH:20]=2)=[O:14])=[N:5][C:6]([O:11]C)=[N:7][C:8]=1[O:9]C)[CH3:2].C(Cl)(=O)C(Cl)=O>C1COCC1>[CH2:1]([C:3]1[C:8](=[O:9])[NH:7][C:6](=[O:11])[NH:5][C:4]=1[C:13]([C:15]1[CH:16]=[C:17]([CH:22]=[CH:23][C:24]#[N:25])[CH:18]=[C:19]([CH3:21])[CH:20]=1)=[O:14])[CH3:2]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 667055223-[3-(5-Ethyl-2,6-dimethoxy-pyrimidine-4-carbonyl)-5-methyl-phenyl]-acrylonitrile

Product 1

HCID 667053953-[3-(5-Ethyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-5-methyl-phenyl]-acrylonitrileYield 22%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-[3-(5-ethyl-2,6-dimethoxy-pyrimidine-4-carbonyl)-5-methyl-phenyl]-acrylonitrile (2.3 g, 6.82 mmol) and oxalyl chloride (10 ml) in anhydrous THF (30 ml) was refluxed for 4 hr. After cooling to room temperature, the mixture was evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, EA:hexanes (1:1)) to afford 460 mg (22%) of a white solid. m.p. 305-306° C.; 1H NMR (200 MHz, DMSO-d6) δ 0.83 (3H, t, J=7.4 Hz), 1.94 (2H, q, J=7.4 Hz), 2.42 (3H, s), 6.65 (1H, d, J=16.8 Hz), 7.72 (1H, d, J=16.8 Hz), 7.80 (1H, s), 7.87 (1H, s), 8.01 (1H, s), 11.08 (1H, s), 11.29 (1H, s); m/z (LC/Mass, EI) 310 (M+H+).

Workup

  1. temperaturewas refluxed for 4 hr
  2. customthe mixture was evaporated in vacuo
  3. customthe residue was purified by silica gel column chromatography (eluent, EA:hexanes (1:1))

Sources & evidence

ORD record
ord-e7e3c894bf0047d2bfaf1fbeb1f62bf8
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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