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

HRID 1355844ノート

反応式

HRID 1355844 の反応式
[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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-33746e70d11440b58b5b0f2de52d1957
出典データセット
uspto-grants-2003_07
特許番号
US06586441B2

反応ノート

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