Acetic Acid → 3-(5-Acetoxy-6-bromohexyl)-1-methyluracil

HRID 361518Notes

Reaction equation

HRID 361518 reaction equation
[OH:1][CH:2]([CH2:16]O)[CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:12](=[O:13])[CH:11]=[CH:10][N:9]([CH3:14])[C:8]1=[O:15].[BrH:18].[C:19]([OH:22])(=O)[CH3:20].C(=O)(O)[O-].[Na+]>ClCCl.O>[C:19]([O:1][CH:2]([CH2:16][Br:18])[CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:12](=[O:13])[CH:11]=[CH:10][N:9]([CH3:14])[C:8]1=[O:15])(=[O:22])[CH3:20]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 232879503-(5,6-Dihydroxyhexyl)-1-methyluracil

Product 1

HCID 232959163-(5-Acetoxy-6-bromohexyl)-1-methyluracilYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-(5,6-dihydroxyhexyl)-1-methyluracil (350 mg, 1.4 mmol) and a 30% solution of hydrogen bromide in acetic acid (0.87 mL, 4.3 mmol) was stirred for 45 minutes. The mixture was then added to a mixture of sodium bicarbonate (1.6 g), water (10 mL) and dichloromethane (20 mL). After 15 minutes of vigorous stirring, the layers were separated and the aqueous layer extracted with dichloromethane (3×40 mL). The combined organic layers were dried over sodium sulfate, then evaporated under vacuum to give 3-(5-acetoxy-6-bromohexyl)-1-methyluracil (500 mg, 100% yield).

Workup

  1. customthe layers were separated
  2. extractionthe aqueous layer extracted with dichloromethane (3×40 mL)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. customevaporated under vacuum

Sources & evidence

ORD record
ord-f2937bff95de41b79f7760afcee9491d
Source dataset
uspto-grants-1999_02
Patent number
US05866576

Reaction notes

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