Potassium Carbonate → HCID 20491763, compound

HRID 434657Notes

Reaction equation

HRID 434657 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5](=[O:8])[NH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[Br:15][CH2:16][CH:17]1[O:19][CH2:18]1>CN(C)C=O>[Br:15][CH2:16][CH:17]([OH:19])[CH2:18][N:4]1[CH:3]=[C:2]([Cl:1])[CH:7]=[N:6][C:5]1=[O:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 18430EpibromohydrinHCID 1085785-Chloro-2(1H)-pyrimidinone

Product 1

HCID 20491763HCID 20491763, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A stirred suspension of 5-chloropyrimidin-2-one (2.610 g), potassium carbonate (55 mg) and 1-bromo-2,3-epoxypropane (3.42 ml) in dry N,N-dimethylformamide (40 ml) was heated at 80° C. After 23/4 h the reaction mixture was evaporated and the residue was subjected to column chromatography on silica developing and eluting with chloroform-ethanol, 19:1. This gave an off white solid which was triturated with ethyl acetate to give white crystals of the title pyrimidinone (1.483 g), m.p. 166°-170° C., λmax (EtOH) 227 nm (ε 9,740).

Workup

  1. customAfter 23/4 h the reaction mixture was evaporated
  2. washeluting with chloroform-ethanol, 19:1
  3. customThis gave an off white solid which
  4. customwas triturated with ethyl acetate

Sources & evidence

ORD record
ord-4b14cda6bd384fbe9788e6d03b7e2765
Source dataset
uspto-grants-1983_08
Patent number
US04399140

Reaction notes

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