N-bromobutanimide → HCID 178517460, compound

HRID 1484840Notes

Reaction equation

HRID 1484840 reaction equation
[C:1]1([C:7]2[N:12]=[C:11]([OH:13])[CH:10]=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C(=O)N([Br:21])C(=O)C1>C(O)(=O)C>[Br:21][C:10]1[C:11]([OH:13])=[N:12][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:8][CH:9]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 178516486HCID 178516486, compound

Product 1

HCID 178517460HCID 178517460, compoundYield 75.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-phenylpyrimidin-4-ol (1.0 g, 5.8 mmol, 1 eq) in acetic acid (20 mL) was added NBS (1.0 g, 5.8 mmol, 1 eq) and heated at 60° C. for 1 h. The reaction solution was concentrated in vacuo and the residue was purified by silica gel chromatography (CH2Cl2/MeOH=97/3 as eluant) to obtain 5-bromo-2-phenylpyrimidin-4-ol (1.1 g, 75.8%) as a white solid. LC-MS (m/z): 251.1 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 7.35-7.51 (m, 3H), 8.10-8.18 (m, 2H), 8.46 (s, 1H), 13.32 (s, 1H).

Workup

  1. concentrationThe reaction solution was concentrated in vacuo
  2. customthe residue was purified by silica gel chromatography (CH2Cl2/MeOH=97/3 as eluant)

Sources & evidence

ORD record
ord-4ba27fb8117e422c9d49bc9cd2fbc94d
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

Loading…