Ammonium formate → 4-(2-Pyrimidinyl)benzenepropanol

HRID 2416533Notes

Reaction equation

HRID 2416533 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[C:7]1[CH:12]=[CH:11][C:10](/[CH:13]=[CH:14]/[CH2:15][OH:16])=[CH:9][CH:8]=1.C([O-])=O.[NH4+]>CO.[Pd]>[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][OH:16])=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 22630896HCID 22630896, compound

Product 1

HCID 226310654-(2-Pyrimidinyl)benzenepropanolYield 79.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (2E)-3-[4-(2-pyrimidinyl)phenyl]-2-propen-1-ol (300 mg, 1.41 mmol, prepared as described in Reference Example 65), ammonium formate (445 mg, 7.06 mmol), and 10% Pd/C (100 mg) in methanol (5 mL) was stirred for 1 h at room temperature. Solids were removed by filtration through Celite and washed with additional methanol (20 mL). The filtrate was concentrated and the residue was taken up in ethyl acetate (30 mL), washed with water (20 mL), dried (MgSO4) and concentrated. Purification by chromatography (SiO2, 1:1 dichloromethane/ethyl acetate) provided 240 mg (79%) of the title compound as a colorless oil. MS 215 (M+H)+.

Workup

  1. customSolids were removed by filtration through Celite
  2. washwashed with additional methanol (20 mL)
  3. concentrationThe filtrate was concentrated
  4. washwashed with water (20 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customPurification by chromatography (SiO2, 1:1 dichloromethane/ethyl acetate)

Sources & evidence

ORD record
ord-38f63379adb142fa80ef844017e2ca08
Source dataset
uspto-grants-2004_11
Patent number
US06825170B2

Reaction notes

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