Sodium Carbonate → 2-amino-6-(2-furyl)-5-nitropyrimidine-4(1H)-one

HRID 1355844노트

반응식

HRID 1355844 반응식
[NH2:1][C:2]1[NH:7][C:6](=[O:8])[C:5]([N+:9]([O-:11])=[O:10])=[C:4](Cl)[N:3]=1.[O:13]1[CH:17]=[CH:16][CH:15]=[C:14]1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[NH2:1][C:2]1[NH:7][C:6](=[O:8])[C:5]([N+:9]([O-:11])=[O:10])=[C:4]([C:14]2[O:13][CH:17]=[CH:16][CH:15]=2)[N:3]=1

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 2734357Furan-2-boronic acidHCID 1354086932-Amino-6-chloro-5-nitro-3,4-dihydropyrimidin-4-one

생성물 1

HCID 1356162012-amino-6-(2-furyl)-5-nitropyrimidine-4(1H)-one수율 44%

시약·촉매·용매 3

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

To a stirred solution of 15.7 g (75.3 mmol) 2-amino-6-chloro-5-nitro-3H-pyrimidin-4-one in 300 ml dioxane and 100 ml water at room temperature were added 8.40 g (75.0 mmol) 2-furylboronic acid, 8.70 g (7.53 mmol) tetrakis(triphenylphosphine)palladium(O) and 150 ml (300 mmol) 2M aqueous sodium carbonate solution. The reaction mixture was heated at reflux for 7 h, then concentrated in vacuo. The residue was resuspended in acetone and the insoluble material collected by filtration. This solid material was then dissolved in 1.21 water and acidified to pH 4-5 with 25% hydrochloric acid. The resulting crystals were collected by filtration and washed with water. After drying in vacuo they were additionally washed with dichloromethane to afford 7.33 g (44%) 2-amino-6-furan-2-yl-5-nitro-3H-pyrimidin-4-one as a yellow crystalline solid. ES-MS m/e (%): 221 ([M—H]−, 100).

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 7 h
  3. concentrationconcentrated in vacuo
  4. filtrationthe insoluble material collected by filtration
  5. dissolutionThis solid material was then dissolved in 1.21 water
  6. filtrationThe resulting crystals were collected by filtration
  7. washwashed with water
  8. customAfter drying in vacuo they
  9. washwere additionally washed with dichloromethane

출처 및 근거

ORD 기록
ord-33746e70d11440b58b5b0f2de52d1957
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06586441B2

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