Stannane, tributyl(1-ethoxyethenyl)- → HCID 18507298, compound

HRID 1356145Notes

Reaction equation

HRID 1356145 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[O:9][C:10](Br)=[CH:11][CH:12]=2)[C:5]([C:14]#[N:15])=[C:4]([S:16][CH3:17])[N:3]=1.[CH2:18]([O:20][C:21]([Sn](CCCC)(CCCC)CCCC)=[CH2:22])[CH3:19]>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[O:9][C:10]([C:18]([O:20][CH2:21][CH3:22])=[CH2:19])=[CH:11][CH:12]=2)[C:5]([C:14]#[N:15])=[C:4]([S:16][CH3:17])[N:3]=1

Participants

5

Reactant 2

HCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 18507285HCID 18507285, compound

Product 1

HCID 18507298HCID 18507298, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of 492 mg (1.58 mmol) 2-amino-4-(5-bromo-furan-2-yl)-6-methylsulfanyl-pyrimidine-5-carbonitrile in 15 ml dioxane under argon at room temperature were added 0.59 ml (1.74 mmol) (I-ethoxyvinyl)tributylstannane and 111 mg (0.16 mmol) bis(triphenylphosphine)palladium(II) chloride. The reaction mixture was heated at 100° C. for 18 h, then cooled to room temperature, 2 g of kieselgel added, and the mixture concentrated in vacuo. Flash chromatography (1/2 ethyl acetate/hexane then 1/1 ethyl acetate/hexane then ethyl acetate) followed by trituration in ether afforded 304 mg (64%) 2-amino-4-[5-(1-ethoxy-vinyl)-furan-2-yl]-6-methylsulfanyl-pyrimidine-5-carbonitrile as an off-white crystalline solid. EI-MS m/e (%): 302 (M+, 88), 273 ([M—C2H5]+, 100), 243 (43), 231 (52).

Workup

  1. temperaturecooled to room temperature
  2. addition2 g of kieselgel added
  3. concentrationthe mixture concentrated in vacuo

Sources & evidence

ORD record
ord-010ec97d674f454880065b011ca9d421
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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