Triphenylarsine → HCID 18507230, compound

HRID 1356106Notes

Reaction equation

HRID 1356106 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[O:19][CH:20]=[CH:21][N:22]=1)CCC.C1([As](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Cu]I>[NH2:1][C:2]1[N:3]=[C:4]([S:11][CH3:12])[C:5]([C:9]#[N:10])=[C:6]([C:18]2[O:19][CH:20]=[CH:21][N:22]=2)[N:7]=1

Participants

7

Reactant 3

HCID 11773TriphenylarsineHCID 154861832-(Tri-n-butylstannyl)oxazoleHCID 187532302-Amino-4-bromo-6-methylsulfanyl-pyrimidine-5-carbonitrile

Product 1

HCID 18507230HCID 18507230, compoundYield 8.1%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

To a stirred solution of 2.37 g (9.67 mmol) 2-amino-4-bromo-6-methylsulfanyl-pyrimidine-5-carbonitrile in 50 ml dry DMF under argon at room temperature were added 4.50 g (12.6 mmol) 2-tributylstannanyl-oxazole, 889 mg (0.97 mmol) tris(dibenzylidene-acetone)dipalladium(O), 1.48 g (4.84 mmol) triphenylarsine and 185 mg (0.97 mmol) copper(I) iodide. The reaction mixture was heated at 95° C. for 48 h, then cooled to room temperature and partitioned between ethyl acetate and water. The phases were separated and the organic phase dried over sodium sulfate and concentrated in vacuo. Flash chromatography (ethyl acetate/hexane 1/1 followed by ethyl acetate) afforded 182 mg (7%) 2-amino-4-methylsulfanyl-6-oxazol-2-yl-pyrimidine-5-carbonitrile as a yellow crystalline solid. ES-MS m/e (%): 234 (M+H+, 100).

Workup

  1. temperaturecooled to room temperature
  2. custompartitioned between ethyl acetate and water
  3. customThe phases were separated
  4. dry with materialthe organic phase dried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8ff21769ec9d4df5a80d4798002010a2
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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