HCID 67131363, compound → 2-Cyclopropylpyrimidin-5-ol

HRID 1926715Notes

Reaction equation

HRID 1926715 reaction equation
C([O:8][C:9]1[CH:10]=[N:11][C:12]([CH:15]2[CH2:17][CH2:16]2)=[N:13][CH:14]=1)C1C=CC=CC=1>CO.[Pd]>[CH:15]1([C:12]2[N:13]=[CH:14][C:9]([OH:8])=[CH:10][N:11]=2)[CH2:17][CH2:16]1

Participants

4

Reactant 1

HCID 67131363HCID 67131363, compound

Product 1

HCID 198710372-Cyclopropylpyrimidin-5-olYield 54%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

5-(Benzyloxy)-2-cyclopropylpyrimidine (4.0 g, 18 mmol) was dissolved in MeOH (100 mL) and 10% palladium on carbon (0.170 g) was added. The mixture was hydrogenated at ambient temperature and 1.013 bar pressure overnight. Filtration and concentration gave a crude product that was filtered through a short silica gel column using 5% MeOH-EtOAc as eluent. Evaporation of the solvent gave 1.3 g (54% yield) of the subtitle compound as a colourless solid.

Workup

  1. customwas hydrogenated at ambient temperature
  2. custom1.013 bar pressure overnight
  3. filtrationFiltration and concentration
  4. customgave a crude product that
  5. filtrationwas filtered through a short silica gel column
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-c37667a588f2416da79dc4e9d8444c97
Source dataset
uspto-grants-2012_05
Patent number
US08183251B2

Reaction notes

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