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

HRID 1355983노트

반응식

HRID 1355983 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

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

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-8c03d03fa4bd4ddb866e8b5291716cb1
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06586441B2

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