Sodium Hydroxide → 5-Bromo-5-(2-ethoxy-ethyl)-pyrimidine-2,4,6-trione

HRID 49149

Reaction equation

HRID 49149 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][CH:6]1[C:11](=[O:12])[NH:10][C:9](=[O:13])[NH:8][C:7]1=[O:14])[CH3:2].[OH-].[Na+].[Br:17]Br>O>[Br:17][C:6]1([CH2:5][CH2:4][O:3][CH2:1][CH3:2])[C:7](=[O:14])[NH:8][C:9](=[O:13])[NH:10][C:11]1=[O:12]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24408BromineHCID 219310235-(2-Ethoxy-ethyl)-pyrimidine-2,4,6-trione

Product 1

HCID 219311235-Bromo-5-(2-ethoxy-ethyl)-pyrimidine-2,4,6-trioneYield 59.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 5-(2-ethoxy-ethyl)-pyrimidine-2,4,6-trione (27.8 g, 139 mmol) and 1.5 L of water was added 1M sodium hydroxide solution (140 mL) and bromine (7.2 mL, 22.2 g, 139 mmol) at 0° C. After warming to room temperature, the mixture was stirred for 48 hours, filtered, and the solids were washed with water, then ether, then hexanes and dried in vacuo, affording 23 g of 5-bromo-5-(2-ethoxy-ethyl)-pyrimidine-2,4,6-trione.

Workup

  1. filtrationfiltered
  2. washthe solids were washed with water
  3. dry with materialether, then hexanes and dried in vacuo

Sources & evidence

ORD record
ord-01d83bd74f01448987ef3d879275010f
Source dataset
uspto-grants-2004_03
Patent number
US06706723B2

Linked notes

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