Water → 1-Benzyloxycarbonylmethyl-2,4-dioxopyrimidine

HRID 23555

Reaction equation

HRID 23555 reaction equation
[O:1]=[C:2]1[NH:7][C:6](=[O:8])[CH:5]=[CH:4][NH:3]1.Br[CH2:10][C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[O:1]=[C:2]1[NH:7][C:6](=[O:8])[CH:5]=[CH:4][N:3]1[CH2:10][C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12]

Participants

6

Reactant 4

HCID 962WaterHCID 1174UracilHCID 11430Potassium CarbonateHCID 62576Benzyl bromoacetate

Product 1

HCID 226011191-Benzyloxycarbonylmethyl-2,4-dioxopyrimidineYield 60.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,4-dioxopyrimidine (1.0 g) in anhydrous DMF (10 ml) were added benzyl bromoacetate (2.5 g) and potassium carbonate (2.5 g). After stirring at room temperature for 15 hours, the reaction mixture was poured into water and extracted with ethyl acetate. The organic phase was washed with brine and then dried with magnesium sulfate, filtered and evaporated under reduced pressure. The precipitate was washed with diethyl ether to give phenylmethyl 2-(2,4-dioxo-1,3-dihydropyrimidinyl)acetate (1.4 g) as a colorless solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with brine
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. washThe precipitate was washed with diethyl ether

Sources & evidence

ORD record
ord-0c6dbf2897d04754b15dfbc2d2793da6
Source dataset
uspto-grants-2005_02
Patent number
US06852744B2

Linked notes

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