Sodium Carbonate → 4-Furan-2-yl-6-methylsulfanyl-5-vinyl-pyrimidin-2-ylamine

HRID 1355983ノート

反応式

HRID 1355983 の反応式
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[C:11](I)=[C:10]([S:13][CH3:14])[N:9]=[C:8]([NH2:15])[N:7]=1.[CH:16]([Sn](CCCC)(CCCC)CCCC)=[CH2:17].C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.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]>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[C:11]([CH:16]=[CH2:17])=[C:10]([S:13][CH3:14])[N:9]=[C:8]([NH2:15])[N:7]=1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 81998TributylvinyltinHCID 185075894-Furan-2-yl-5-iodo-6-methylsulfanyl-pyrimidin-2-ylamine

生成物 1

HCID 185074684-Furan-2-yl-6-methylsulfanyl-5-vinyl-pyrimidin-2-ylamine収率 66%

試薬・触媒・溶媒 2

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

実験手順

To a stirred solution of 1.00 g (3.00 mmol) 4-furan-2-yl-5-iodo-6-methylsulfanyl-pyrimidin-2-yl-amine in 30 ml dioxane under argon at room temperature were added 0.96 ml (3.30 mmol) vinyltributylstannane, 347 mg (0.30 mmol) tetrakis(triphenylphosphine) palladium(O) and 6.0 ml (12.0 mmol) 2M aqueous sodium carbonate solution. The reaction mixture was heated at reflux for 16 h, then cooled to room temperature, 3 g of kieselgel added, and the mixture concentrated in vacuo. Flash chromatography (1/3 ethyl acetate/hexane) followed trituration in ether/hexane afforded 460mg (66%) 4-furan-2-yl-6-methylsulfanyl-5-vinyl-pyrimidin-2-ylamine as an orange crystalline solid. EI-MS m/e (%): 233 (M+, 48), 218 ([M—CH3]+, 76), 216 ([M—NH3]+, 46), 125 (100).

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 16 h
  3. addition3 g of kieselgel added
  4. concentrationthe mixture concentrated in vacuo

出典と根拠

ORDレコード
ord-8c03d03fa4bd4ddb866e8b5291716cb1
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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