Methyl 6-methyl-2-phenyl-4-(3-nitrophenyl)-5-pyrimidinecarboxylate → Methyl 6-bromomethyl-4-(3-nitrophenyl)-2-phenyl-5-pyrimidinecarboxylate

HRID 4682

Reaction equation

HRID 4682 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[C:3]=1[C:23]([O:25][CH3:26])=[O:24].C1C=C[NH+]=CC=1.[Br:33][Br-]Br.Br.C(O)(=O)C>C(O)(=O)C>[Br:33][CH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[C:3]=1[C:23]([O:25][CH3:26])=[O:24]

Participants

4

Reactant 2

HCID 15147475Methyl 6-methyl-2-phenyl-4-(3-nitrophenyl)-5-pyrimidinecarboxylateHCID 21893785Acetic Acid Mixture with Hydrobromic Acid

Product 1

HCID 10410300Methyl 6-bromomethyl-4-(3-nitrophenyl)-2-phenyl-5-pyrimidinecarboxylateYield 66.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of methyl 6-methyl-4-(3-nitrophenyl)-2-phenyl-5-pyrimidinecarboxylate (5 g), pyridinium bromide perbromide (5.6 g) and 25% hydrogen bromide-acetic acid (5 ml) in acetic acid (200 ml) was stirred for 2 hours at room temperature. The reaction mixture was poured into ice water (200 ml) and stirred for 10 minutes. The resulting precipitates were collected and dissolved in a mixture of chloroform (50 ml) and water (50 ml). The separated organic layer was washed with saturated aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride successively, dried over magnesium sulfate. The solvent was evaporated in vacuo and the residual crystal was recrystallized from ethanol to give methyl 6-bromomethyl-4-(3-nitrophenyl)-2-phenyl-5-pyrimidinecarboxylate (4.07 g).

Workup

  1. stirringstirred for 10 minutes
  2. customThe resulting precipitates
  3. customwere collected
  4. dissolutiondissolved in a mixture of chloroform (50 ml) and water (50 ml)
  5. washThe separated organic layer was washed with saturated aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride successively
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was evaporated in vacuo
  8. customthe residual crystal was recrystallized from ethanol

Sources & evidence

ORD record
ord-dcd8d2b7abf04ce0bdd51fdc309fc6a6
Source dataset
uspto-grants-1988_02
Patent number
US04727073

Linked notes

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