N-bromobutanimide → 5-Bromo-2,6-diphenylpyrimidin-4-ol

HRID 1447

Reaction equation

HRID 1447 reaction equation
[C:1]1([C:7]2[NH:12][C:11](=[O:13])[CH:10]=[C:9]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:20]N1C(=O)CCC1=O>C(O)(=O)C>[Br:20][C:10]1[C:11](=[O:13])[NH:12][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:8][C:9]=1[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 1354755602,6-Diphenylpyrimidin-4-ol

Product 1

HCID 1354674325-Bromo-2,6-diphenylpyrimidin-4-olYield 48.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a suspension of 13.37 g (56 mmol) of 2,6-diphenyl-4(3H)-pyrimidinone and 200 mL glacial acetic acid was added 15.1 g (84.8 mmol) of N-bromosuccinimide and the mixture was left to stir at room temperature for 60 h. The reaction was poured onto 100 g crushed ice and vacuum filtered, washing well with water, then air dried to yield 8.85 g (48%) 5-bromo-2,6-diphenyl-4(3H)-pyrimidinone, as a white solid. 1H-NMR (d6DMSO) δ 7.55(6H,m); 7.75(2H,m); 8.15(2H,m).

Workup

  1. waitthe mixture was left
  2. additionThe reaction was poured onto 100 g
  3. customcrushed ice and vacuum
  4. filtrationfiltered
  5. washwashing well with water
  6. customair dried

Sources & evidence

ORD record
ord-f05000905bc748e98487d679b80f953b
Source dataset
uspto-grants-1998_03
Patent number
US05726124

Linked notes

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