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

HRID 1355983Notes

Reaction equation

HRID 1355983 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-8c03d03fa4bd4ddb866e8b5291716cb1
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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