N-bromobutanimide → 5-bromo-6-chloromethyluracil

HRID 2194597Notes

Reaction equation

HRID 2194597 reaction equation
[Cl:1][CH2:2][C:3]1[NH:8][C:7](=[O:9])[NH:6][C:5](=[O:10])[CH:4]=1.C1C(=O)N([Br:18])C(=O)C1>CN(C=O)C>[Br:18][C:4]1[C:5](=[O:10])[NH:6][C:7](=[O:9])[NH:8][C:3]=1[CH2:2][Cl:1]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 732736-(Chloromethyl)-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 109335915-bromo-6-chloromethyluracilYield 78.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 6-(chloromethyl)uracil (2.0 g, 12.5 mmol) in DMF (15 mL) at 0° C. was added NBS (recrystallized, 2.44 g, 13.7 mmol). The mixture was stirred at 0° C. for 1.5 h, and then quenched by ice water. The precipitate was collected by filtration and washed with AcOH and water to give the title compound (2.35 g, 69%) as a white solid. 1H NMR (DMSO, 500 MHz) δ 1.66 (s, 1H), δ 11.61 (s, 1H), δ 4.47 (s, 2H). MS (Multimode, M+H+) C5H5BrClN2O2, calcd. 238.9. found 238.9.

Workup

  1. customquenched by ice water
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with AcOH and water

Sources & evidence

ORD record
ord-ded63685c8c1418584cdb4fc3ad37adc
Source dataset
uspto-grants-2012_12
Patent number
US08334292B1

Reaction notes

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