2-(Tributylstannyl)pyrazine → 2-Amino-4-methylsulfanyl-6-pyrazin-2-yl-pyrimidine-5-carbonitrile

HRID 1356185Notes

Reaction equation

HRID 1356185 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]=[N:22][CH:21]=[CH:20][N:19]=1)CCC>CN(C=O)C.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.[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]=[N:22][CH:21]=[CH:20][N:19]=2)[N:7]=1

Participants

6

Reactant 2

HCID 27373162-(Tributylstannyl)pyrazineHCID 187532302-Amino-4-bromo-6-methylsulfanyl-pyrimidine-5-carbonitrile

Product 1

HCID 185072312-Amino-4-methylsulfanyl-6-pyrazin-2-yl-pyrimidine-5-carbonitrileYield 31.2%

Reagents, catalysts & solvents 3

HCID 14829Copper oxideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 1.11 g (4.52 mmol) 2-amino-4-bromo-6-methylsulfanyl-pyrimidine-5-carbonitrile in 10 ml dry DMF under argon at room temperature were added 2.00 g (5.42 mmol) 2-(tri-n-butylstannanyl)pyrazine, 190 mg (0.27 mmol) bis(triphenylphosphine)palladium(II) chloride and 431 mg (5.42 mmol) copper(II) oxide. The reaction mixture was heated at reflux for 18 h, then cooled to room temperature and concentrated in vacuo. Flash chromatography (ethyl acetate/hexane 1/1 then ethyl acetate) afforded 344 mg (31%) 2-amino-4-methylsulfanyl-6-pyrazin-2-yl-pyrimidine-5-carbonitrile as an off-white crystalline solid. EI-MS m/e (%): 244 (M+, 100), 243 ([M—H]+, 40), 190 (55).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 18 h
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-73db198b83724da2a9742c35382ff0c4
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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