Benzyl Chloride → 3-benzyl-6-(benzyloxy)-pyrimidin-4(3H)-one

HRID 350890Notes

Reaction equation

HRID 350890 reaction equation
O[C:2]1[CH:7]=[C:6]([OH:8])[N:5]=[CH:4][N:3]=1.[C:9](=[O:12])([O-])[O-].[K+].[K+].[CH2:15](Cl)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN(C)C=O>[CH2:15]([N:5]1[C:6](=[O:8])[CH:7]=[C:2]([O:12][CH2:9][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:3]=[CH:4]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 178516651HCID 178516651, compound

Product 1

HCID 210890133-benzyl-6-(benzyloxy)-pyrimidin-4(3H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4,6-dihydroxypyrimidine (25.0 g, 0.223 mol) and potassium carbonate (65.1 g, 0.471 mol) are combined in 0.5 L anhydrous dimethylformamide. Benzyl chloride (55.7 g, 0.439 mol) is added dropwise over 30 minutes with stirring. After 4 h the solution is filtered, and the filtrate concentrated in vacuo. The residue is washed with acetonitrile, and the product is collected as a white solid by filtration (44.6 g, 68%). 1H-NMR (400 MHz, DMSO-d6) δ 8.06 (m, 2 H), 7.61 (quartet, J=8.45 Hz, 1H), 7.30 (t, J=10.37 Hz, 1H), 7.12, (t, J=8.45 Hz, 1H), 7.09 (d, J=5.06 Hz, 2H), 5.14 (s, 2H). LC/MS tr=5.29 minutes (0–95% acetonitrile/water, 0.05% trifluoroacetic acid, over 6 minutes at 1 ml/min with detection at 215 nm, at 50° C.) ES-MS m/z 293 (M+H).

Workup

  1. filtrationAfter 4 h the solution is filtered
  2. concentrationthe filtrate concentrated in vacuo
  3. washThe residue is washed with acetonitrile
  4. filtrationthe product is collected as a white solid by filtration (44.6 g, 68%)
  5. customLC/MS tr=5.29 minutes (0–95% acetonitrile/water, 0.05% trifluoroacetic acid, over 6 minutes at 1 ml/min with detection at 215 nm, at 50° C.) ES-MS m/z 293 (M+H)

Sources & evidence

ORD record
ord-e0ffdeb547244e4ab5ef28c219fcbc37
Source dataset
uspto-grants-2007_02
Patent number
US07183287B2

Reaction notes

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