4-Furan-2-yl-6-methylsulfanyl-5-vinyl-pyrimidin-2-ylamine → 5-Ethyl-4-furan-2-yl-6-methylsulfanyl-pyrimidin-2-ylamine

HRID 1355984Notes

Reaction equation

HRID 1355984 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[C:11]([CH:12]=[CH2:13])=[C:10]([S:14][CH3:15])[N:9]=[C:8]([NH2:16])[N:7]=1.[H][H]>C(O)C.[Pd]>[CH2:12]([C:11]1[C:6]([C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)=[N:7][C:8]([NH2:16])=[N:9][C:10]=1[S:14][CH3:15])[CH3:13]

Participants

5

Reactant 2

HCID 185074684-Furan-2-yl-6-methylsulfanyl-5-vinyl-pyrimidin-2-ylamineHCID 178418361HCID 178418361, compound

Product 1

HCID 185072405-Ethyl-4-furan-2-yl-6-methylsulfanyl-pyrimidin-2-ylamineYield 30%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 200 mg (0.86 mmol) 4-furan-2-yl-6-methylsulfanyl-5-vinyl-pyrimidin-2-ylamine in 30 ml ethanol was stirred with a spatula end of 10% palladium on charcoal under 1 atm of hydrogen for 16 h at room temperature. After filtration to remove the catalyst, the reaction mixture was concentrated in vacuo and the residue triturated in ether/hexane to afford 60 mg (30%) 5-ethyl-4-furan-2-yl-6-methylsulfanyl-pyrimidin-2-ylamine as an off-white crystalline solid. ES-MS rn/e (%): 236 (M+H+, 100).

Workup

  1. filtrationAfter filtration
  2. customto remove the catalyst
  3. concentrationthe reaction mixture was concentrated in vacuo
  4. customthe residue triturated in ether/hexane

Sources & evidence

ORD record
ord-c39b0dae3e594ae595ea55b95d6889ba
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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