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 426170노트

반응식

HRID 426170 반응식
[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]

참가 물질

4

반응물 1

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

생성물 1

HCID 667053903-[3-(5-Isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-5-methyl-phenyl]-acrylonitrile수율 55%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 65578Oxalyl chloride용매

실험 절차

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 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+).

후처리

  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))

출처 및 근거

ORD 기록
ord-8647082309ae4ca78220a5b849fc5f1e
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08106064B2

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