Formic Acid → HCID 19702798, compound

HRID 861396Notes

Reaction equation

HRID 861396 reaction equation
C(N(CC)CC)C.C(O)=O.C(OC([CH:17]([C:27](=[O:30])[CH2:28][CH3:29])[C:18]([C:20]1[C:21]([CH3:26])=[N:22][CH:23]=[N:24][CH:25]=1)=[O:19])=O)C=C>C1COCC1.C([O-])(=O)C.C([O-])(=O)C.[Pd+2]>[CH3:26][C:21]1[C:20]([C:18](=[O:19])[CH2:17][C:27](=[O:30])[CH2:28][CH3:29])=[CH:25][N:24]=[CH:23][N:22]=1

Participants

6

Reactant 3

HCID 284Formic AcidHCID 8471TriethylamineHCID 19702801HCID 19702801, compound

Product 1

HCID 19702798HCID 19702798, compoundYield 101.7%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 6.6 mg of palladium diacetate (Pd(OAc)2), triethylamine (226 mg), and formic acid (204 mg) in 2 ml THF was added 410 mg of 2-(allyloxycarbonyl)-1-(4-methylpyrimidin-5-yl)pentan-1,3-dione. The mixture was refluxed for 3.5 hours, cooled and partitioned between ethyl acetate and water. The organic layer was dried with magnesium sulfate, filtered and evaporated to yield 290 mg of 1-(4-methylpyrimidin-5-yl)pentan-1,3-dione as an amber liquid.

Workup

  1. temperatureThe mixture was refluxed for 3.5 hours
  2. temperaturecooled
  3. custompartitioned between ethyl acetate and water
  4. dry with materialThe organic layer was dried with magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-71ae2b67e5684565beb59f4f65d8e2cd
Source dataset
uspto-grants-1998_02
Patent number
US05714438

Reaction notes

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