Sodium Carbonate → 5-(2,4-Dimethyl-oxazol-5-yl)-2,4-dimethoxy-pyrimidine

HRID 12690

Reaction equation

HRID 12690 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([O:9][CH3:10])[C:6](B(O)O)=[CH:5][N:4]=1.I[C:15]1[O:19][C:18]([CH3:20])=[N:17][C:16]=1[CH3:21].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]>[CH3:20][C:18]1[O:19][C:15]([C:6]2[C:7]([O:9][CH3:10])=[N:8][C:3]([O:2][CH3:1])=[N:4][CH:5]=2)=[C:16]([CH3:21])[N:17]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 2736209(2,4-Dimethoxypyrimidin-5-yl)boronic acidHCID 593375895-Iodo-2,4-dimethyl-oxazole

Product 1

HCID 589942085-(2,4-Dimethyl-oxazol-5-yl)-2,4-dimethoxy-pyrimidineYield 67.1%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 10311-PropanolSolvent

Procedure

2,4-Dimethoxy-pyrimidine-5-boronic acid (840 mg, 4.6 mmol) was dissolved in degassed n-PrOH (40 mL) and then 5-iodo-2,4-dimethyl-oxazole (Prep60, 850 mg, 3.8 mmol), Na2CO3 (848 mg, 8 mmol), PPh3 (332 mg, 1.3 mmol) and Pd(OAc)2 (85 mg, 0.38 mmol) were added. The suspension was stirred at reflux for 4 hours. The solvent was evaporated under vacuum and the crude was partitioned between water and ethyl acetate. The organic phase was dried (Na2SO4) and evaporated. The crude was purified by SCX cartridge to give 600 mg of the title compound (66% yield).

Workup

  1. temperatureat reflux for 4 hours
  2. customThe solvent was evaporated under vacuum
  3. customthe crude was partitioned between water and ethyl acetate
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. customevaporated
  6. customThe crude was purified by SCX cartridge

Sources & evidence

ORD record
ord-49aa7eb002944783b9f978f9c7b080b9
Source dataset
uspto-grants-2010_06
Patent number
US07727988B2

Linked notes

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