Stannane, tributyl(1-ethoxyethenyl)- → HCID 18507607, compound

HRID 1356084Notes

Reaction equation

HRID 1356084 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](Br)[C:5]([C:9]#[N:10])=[C:4]([S:11][CH3:12])[N:3]=1.[CH2:13]([O:15][C:16]([Sn](CCCC)(CCCC)CCCC)=[CH2:17])[CH3:14]>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:13]([O:15][CH2:16][CH3:17])=[CH2:14])[C:5]([C:9]#[N:10])=[C:4]([S:11][CH3:12])[N:3]=1

Participants

5

Reactant 2

HCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 187532302-Amino-4-bromo-6-methylsulfanyl-pyrimidine-5-carbonitrile

Product 1

HCID 18507607HCID 18507607, compoundYield 48.6%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 300 mg (1.22 mmol) 2-amino-4-bromo-6-methylsulfanyl-pyrimidine-5-carbonitrile in 10 ml dioxane under argon at room temperature were added 0.41 ml (1.22 mmol) (1-ethoxyvinyl)tributylstannane and 86 mg (0.12 mmol) bis(triphenyl-phosphine)palladium(II) chloride. The reaction mixture was heated at reflux for 16 h, then cooled to room temperature, 2 g of kieselgel added, and the mixture concentrated in vacuo. Flash chromatography (hexane then 1/1 ethyl acetate/hexane) followed by trituration in ether/hexane afforded 140 mg (48%) 2-amino-4-(1-ethoxy-vinyl)-6-methylsulfanyl-pyrimidine-5-carbonitrile as a white crystalline solid. EI-MS m/e (%): 236 (M+, 17), 221 ([M—CH3]+, 61), 207 ([M—C2H5]+, 32), 192 ([M—C3H8]+, 100).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 16 h
  3. addition2 g of kieselgel added
  4. concentrationthe mixture concentrated in vacuo

Sources & evidence

ORD record
ord-e376cbfd174a4b3585f2f19aa95259b8
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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