Sodium Carbonate → 2,4-Ditert-butoxy-5-(3-methyl-2-thienyl)pyrimidine

HRID 12660Notes

Reaction equation

HRID 12660 reaction equation
[C:1]([O:5][C:6]1[N:11]=[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[C:9](B(O)O)=[CH:8][N:7]=1)([CH3:4])([CH3:3])[CH3:2].Br[C:21]1[S:22][CH:23]=[CH:24][C:25]=1[CH3:26].C([O-])([O-])=O.[Na+].[Na+].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(O)CC.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:1]([O:5][C:6]1[N:11]=[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[C:9]([C:21]2[S:22][CH:23]=[CH:24][C:25]=2[CH3:26])=[CH:8][N:7]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 843142-Bromo-3-methylthiopheneHCID 2735950(2,4-Di-tert-butoxypyrimidin-5-yl)boronic acid

Product 1

HCID 44586132,4-Ditert-butoxy-5-(3-methyl-2-thienyl)pyrimidineYield 32%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 10311-PropanolSolvent

Procedure

2,4-Di-tert-butoxy-pyrimidine-5-boronic acid (500 mg, 1.75 mmol) was dissolved in n-PrOH (5 mL) and then 2-bromo-3-methylthiophene (236 μl, 2.1 mmol), Na2CO3 (556 mg, 5.25 mmol), PPh3 (133 mg, 0.52 mmol) and Pd(OAc)2 (40 mg, 0.17 mmol) were added. The suspension was stirred at reflux for 2.5 hours. The solvent was evaporated and the crude was dissolved in water and extracted with Et2O. The organic phase was dried (Na2SO4) and evaporated. The crude was purified by flash chromatography with ethyl acetate-petroleum ether (1-99) to give 170 mg of the title compound as a white solid (32% yield).

Workup

  1. temperatureat reflux for 2.5 hours
  2. customThe solvent was evaporated
  3. dissolutionthe crude was dissolved in water
  4. extractionextracted with Et2O
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. customevaporated
  7. customThe crude was purified by flash chromatography with ethyl acetate-petroleum ether (1-99)

Sources & evidence

ORD record
ord-6a27ead10db740a4ac7fefbba65f9c12
Source dataset
uspto-grants-2010_06
Patent number
US07727988B2

Reaction notes

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