Ammonium formate → HCID 22630777, compound

HRID 2416553Notes

Reaction equation

HRID 2416553 reaction equation
[CH3:1][O:2][CH:3]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[N:19]=[CH:18][CH:17]=[CH:16][N:15]=3)=[CH:10][CH:9]=2)=[CH:6][CH:5]([O:20][CH3:21])[O:4]1.C([O-])=O.[NH4+]>CO.[Pd]>[CH3:1][O:2][CH:3]1[CH:7]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[N:15]=[CH:16][CH:17]=[CH:18][N:19]=3)=[CH:10][CH:9]=2)[CH2:6][CH:5]([O:20][CH3:21])[O:4]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 22631085HCID 22631085, compound

Product 1

HCID 22630777HCID 22630777, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2,5-dihydro-2,5-dimethoxy-3-[4-(pyrimidin-2-yl)phenyl]furan (70 mg, 0.25 mmol), 10% Pd/C (20 mg), and ammonium formate (46 mg, 0.75 mmol) in methanol (1 mL) was stirred overnight. The reaction mixture was filtered through a fritted funnel, and concentrated in vacuo. The crude product was partitioned between ethyl acetate and sat. aq. NaHCO3, the organic layer dried with Na2SO4, and concentrated in vacuo to give 60 mg (85%) of the title compound, which was used without further purification. MS 287 (M+H)+.

Workup

  1. filtrationThe reaction mixture was filtered through a fritted funnel
  2. concentrationconcentrated in vacuo
  3. customThe crude product was partitioned between ethyl acetate and sat. aq. NaHCO3
  4. dry with materialthe organic layer dried with Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1ae37e00f33a4bd8ae66a14bc206afee
Source dataset
uspto-grants-2004_11
Patent number
US06825170B2

Reaction notes

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