2-(Tributylstannyl)pyridine → HCID 18507249, compound

HRID 1356085Notes

Reaction equation

HRID 1356085 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.C([Sn](CCCC)(CCCC)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)CCC>CN(C=O)C.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cu]=O>[NH2:1][C:2]1[N:3]=[C:4]([S:11][CH3:12])[C:5]([C:9]#[N:10])=[C:6]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[N:7]=1

Participants

6

Reactant 2

HCID 6077842-(Tributylstannyl)pyridineHCID 187532302-Amino-4-bromo-6-methylsulfanyl-pyrimidine-5-carbonitrile

Product 1

HCID 18507249HCID 18507249, compoundYield 20.1%

Reagents, catalysts & solvents 3

HCID 14829Copper oxideCatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of 600 mg (2,45 mmol) 2-amino-4-bromo-6-methylsulfanyl-pyrimidine-5-carbonitrile in 12 ml dry DMF under argon at room temperature were added 1.08 g (2.94 mmol) 2-(tributylstannyl)pyridine, 86 mg (0.12 mmol) bis(triphenylphosphine) palladium(II) chloride and 195 mg (2,45 mmol) copper(II) oxide. The reaction mixture was heated at 100° C. for 16 h, then cooled to room temperature, 2 g of kieselgel added, and the mixture concentrated in vacuo. Flash chromatography (hexane then 1/8 ethyl acetate/hexane) followed by trituration in ether/hexane afforded 120 mg (20%) 2-amino-4-methylsulfanyl-6-pyridin-2-yl-pyrimidine-5-carbonitrile as an off-white crystalline solid. EI-MS m/e (%): 243 (M+, 95), 242 ([M—H]+, 100).

Workup

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

Sources & evidence

ORD record
ord-354a3f78978b43f18e3fbd7a6abedb46
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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