Potassium Carbonate → 6-Benzyloxy-3-[2-(4-hydroxymethyl-phenyl)-ethyl]-3H-pyrimidin-4-one

HRID 564163Notes

Reaction equation

HRID 564163 reaction equation
[CH2:1]([O:8][C:9]1[N:14]=[CH:13][NH:12][C:11](=[O:15])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][OH:26])=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:1]([O:8][C:9]1[N:14]=[CH:13][N:12]([CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([CH2:25][OH:26])=[CH:21][CH:20]=2)[C:11](=[O:15])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 210901216-benzyloxy-3H-pyrimidin-4-oneHCID 53929068[4-(2-Chloroethyl)phenyl]methanol

Product 1

HCID 670074186-Benzyloxy-3-[2-(4-hydroxymethyl-phenyl)-ethyl]-3H-pyrimidin-4-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To 3.00 g (14.8 mmol) 6-benzyloxy-3H-pyrimidin-4-one in 15 mL DMF is added 2.66 g (15.6 mmol) [4-(2-chloro-ethyl)-phenyl]-methanol (preparation 1b) and 5.13 g (37.1 mmol) potassium carbonate. The reaction mixture is stirred 3 h at 100° C., filtered and the solvent is evaporated. The residue is put on silica gel and is purified by chromatography (silica gel; PE/EtOAc 1:1 to 2.5:7.5)

Workup

  1. filtrationfiltered
  2. customthe solvent is evaporated
  3. customis purified by chromatography (silica gel; PE/EtOAc 1:1 to 2.5:7.5)

Sources & evidence

ORD record
ord-e229cbf82fe74a95b488eeb9e4898305
Source dataset
uspto-grants-2011_11
Patent number
US08067590B2

Reaction notes

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