Benzyl Alcohol → 5-(benzyloxy)-3-(methoxymethyl)-2,6-dimethylpyrimidin-4(3H)-one

HRID 2387749Notes

Reaction equation

HRID 2387749 reaction equation
I[C:2]1[C:3](=[O:13])[N:4]([CH2:10][O:11][CH3:12])[C:5]([CH3:9])=[N:6][C:7]=1[CH3:8].C(=O)([O-])[O-].[Cs+].[Cs+].N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.[CH2:34]([OH:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C.[Cu](I)I>[CH2:34]([O:41][C:2]1[C:3](=[O:13])[N:4]([CH2:10][O:11][CH3:12])[C:5]([CH3:9])=[N:6][C:7]=1[CH3:8])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

8

Reactant 4

HCID 244Benzyl AlcoholHCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 674740695-iodo-3-(methoxymethyl)-2,6-dimethylpyrimidin-4(3H)-one

Product 1

HCID 672837945-(benzyloxy)-3-(methoxymethyl)-2,6-dimethylpyrimidin-4(3H)-one

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The compound 326-3 (4.78 g) was dissolved in toluene (130 ml). Cesium carbonate (10.6 g), 1,10-phenanthroline (4.41 g) and copper iodide (3.1 g) were added to the solution, and the obtained mixture was stirred for 5 minutes. Thereafter, benzyl alcohol (5.28 ml) was added to the reaction mixture. The obtained mixture was stirred at 110° C. for 5 days. The reaction mixture was diluted with ethyl acetate and filtered. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (n-heptane:ethyl acetate=19:1 to 1:2), so as to obtain the title compound (1.42 g).

Workup

  1. stirringThe obtained mixture was stirred at 110° C. for 5 days
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe obtained residue was purified by silica gel column chromatography (n-heptane:ethyl acetate=19:1 to 1:2)

Sources & evidence

ORD record
ord-875b999a5f9b4523b55a641e961fcdaa
Source dataset
uspto-grants-2012_09
Patent number
US08268848B2

Reaction notes

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