Sodium Carbonate → HCID 29153134, compound

HRID 1514427Notes

Reaction equation

HRID 1514427 reaction equation
I[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=1.[CH3:10][C:11]1[C:15](B(O)O)=[C:14]([CH3:19])[O:13][N:12]=1.C([O-])([O-])=O.[Na+].[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(O)CC.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:10][C:11]1[C:15]([C:2]2[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=2)=[C:14]([CH3:19])[O:13][N:12]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 27343463,5-Dimethylisoxazole-4-boronic acidHCID 38589014-Iodo-2-(methylthio)pyrimidine

Product 1

HCID 29153134HCID 29153134, compoundYield 97.7%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 10311-PropanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-iodo-2-methylsulfanyl-pyrimidine (745 mg, 2.95 mmol) in degassed nPrOH (55 ml), 3,5-dimethyl-isoxazole-4-boronic acid (500 mg, 3.54 mmol), Na2CO3 (375 mg, 3.54 mmol), triphenylphosphine (80 mg, 0.29 mmol) and Pd(OAc)2 (20 mg, 0.09 mmol) were added. The mixture was stirred at 100° C. for 4.5 hours. The solvent was evaporated under vacuum, and the crude was dissolved in DCM and washed with water. The organic phase was dried (Na2SO4) and evaporated. The crude was purified by flash chromatography with petroleum ether-ethyl acetate (95-5 to 9-1) to give 638 mg of the title compound (97% yield).

Workup

  1. customThe solvent was evaporated under vacuum
  2. dissolutionthe crude was dissolved in DCM
  3. washwashed with water
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. customevaporated
  6. customThe crude was purified by flash chromatography with petroleum ether-ethyl acetate (95-5 to 9-1)

Sources & evidence

ORD record
ord-8a20d38af7a942988153cf882a1ce3bf
Source dataset
uspto-grants-2012_07
Patent number
US08222266B2

Reaction notes

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