Sodium hydride → 1-Benzyloxycarbonylmethyl-3-(tert-butoxycarbonylmethyl)-2,4-dioxopyrimidine

HRID 23556Notes

Reaction equation

HRID 23556 reaction equation
[O:1]=[C:2]1[NH:7][C:6](=[O:8])[CH:5]=[CH:4][N:3]1[CH2:9][C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11].[H-].[Na+].Br[CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25].[Cl-].[NH4+]>CN(C=O)C>[C:27]([O:26][C:24]([CH2:23][N:7]1[C:6](=[O:8])[CH:5]=[CH:4][N:3]([CH2:9][C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[C:2]1=[O:1])=[O:25])([CH3:30])([CH3:29])[CH3:28]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 79177tert-Butyl bromoacetateHCID 226011191-Benzyloxycarbonylmethyl-2,4-dioxopyrimidine

Product 1

HCID 226011081-Benzyloxycarbonylmethyl-3-(tert-butoxycarbonylmethyl)-2,4-dioxopyrimidineYield 83.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of phenylmethyl 2-(2,4-dioxo-1,3-dihydropyrimidinyl)acetate (1.0 g) in anhydrous DMF (10 ml) at 0° C. was added portionwise sodium hydride (0.18 g). After the reaction mixture was stirred for 15 minutes with cooling in an ice bath, tert-butyl bromoacetate (0.9 g) was added. After stirring the mixture at room temperature for 1 hour, to the reaction mixture was added saturated aqueous ammonium chloride solution, and the reaction mixture was extracted with ethyl acetate. The organic phase was washed with brine and dried over magnesium sulfate, filtered and evaporated under reduced pressure. The residue was purified by column chromatography (silica gel, n-hexane:ethyl acetate 2:1) to give phenylmethyl 2-(3-{[(tert-butyl)oxycarbonyl]methyl}-2,4-dioxo-1,3-dihydropyrimidinyl)acetate (1.2 g) as a colorless oil.

Workup

  1. temperaturewith cooling in an ice bath
  2. stirringAfter stirring the mixture at room temperature for 1 hour
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. washThe organic phase was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe residue was purified by column chromatography (silica gel, n-hexane:ethyl acetate 2:1)

Sources & evidence

ORD record
ord-6c72b8916c854307bd2a3c4f7ae92f23
Source dataset
uspto-grants-2005_02
Patent number
US06852744B2

Reaction notes

Loading…