N-bromobutanimide → HCID 178442491, compound

HRID 2364913Notes

Reaction equation

HRID 2364913 reaction equation
[CH2:1]([C:7]1[CH:12]=[C:11]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[N:10]=[C:9]([OH:19])[N:8]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[Br:20]N1C(=O)CCC1=O>CN(C)C=O>[Br:20][C:12]1[C:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])=[N:8][C:9]([OH:19])=[N:10][C:11]=1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 178442370HCID 178442370, compound

Product 1

HCID 178442491HCID 178442491, compoundYield 20.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4,6-dihexylpyrimidin-2-ol (31.2 g, 118 mmol) was dissolved in 375 mL of dimethylformamide, and 21.0 g (118 mmol) of N-bromo-succinimide was added at 3° C., and the mixture was stirred for 2.5 hours. Ice water (500 g) was added, and the mixture was extracted with ethyl acetate, washed with saturated saline, dried over magnesium sulfate and concentrated. The concentrate was purified by re-crystallization from ethanol, and the purity thereof was enhanced by a silica gel column (hexane•ethyl acetate) to obtain 8.4 g (24 mmol) of 5-bromo-4,6-dihexylpyrimidin-2-ol.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washwashed with saturated saline
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe concentrate was purified by re-crystallization from ethanol

Sources & evidence

ORD record
ord-caefbcb28c7d4d0bb2dfbcff04f0024c
Source dataset
uspto-grants-2014_04
Patent number
US08697256B2

Reaction notes

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