Water → 1-((benzyloxy)methyl)pyrimidine-2,4(1H,3H)-dione

HRID 1838432Notes

Reaction equation

HRID 1838432 reaction equation
[NH:1]1[CH:6]=[CH:5][C:4](=[O:7])[NH:3][C:2]1=[O:8].[CH2:9]([O:16][CH2:17]Cl)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.O>ClCCl.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:9]([O:16][CH2:17][N:1]1[CH:6]=[CH:5][C:4](=[O:7])[NH:3][C:2]1=[O:8])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 962WaterHCID 1174UracilHCID 137983Benzyl chloromethyl ether

Product 1

HCID 130164351-((benzyloxy)methyl)pyrimidine-2,4(1H,3H)-dioneYield 86.1%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6344DichloromethaneSolvent

Procedure

After N,O-bis(trimethylsilyl)acetoamide (18.5 ml, 74.8 mmol) was added dropwise to a suspension of pyrimidine-2,4-dione (3.36 g, 30.0 mmol) in dichloromethane (90 ml) at room temperature, the mixture was stirred for 2 hours. Tetra-n-butyl ammonium iodide (1.12 g, 3.0 mmol) was added to the reaction mixture, and benzyloxymethyl chloride (4.4 ml, 31.7 mmol) was further added to it. This mixture was stirred at room temperature for 3 hours. The reaction mixture was neutralized with water and a saturated aqueous solution of sodium hydrogencarbonate, and it was extracted with ethyl acetate. The organic layer was washed with a 10% aqueous solution of sodium thiosulfate and with water successively, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The solid residue was washed with diisopropyl ether and collected by filtration to give the title compound (6.00 g, yield 86%) as a white powder.

Workup

  1. additionwas further added to it
  2. stirringThis mixture was stirred at room temperature for 3 hours
  3. extractiona saturated aqueous solution of sodium hydrogencarbonate, and it was extracted with ethyl acetate
  4. washThe organic layer was washed with a 10% aqueous solution of sodium thiosulfate and with water successively
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. washThe solid residue was washed with diisopropyl ether
  8. filtrationcollected by filtration

Sources & evidence

ORD record
ord-095be05acd744f78b9aa93d6b79d169e
Source dataset
uspto-grants-2004_01
Patent number
US06673804B1

Reaction notes

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