Sodium Hydroxide → 4-(4-Bromophenyl)-2-phenyl-6-(pyridin-2-yl)pyrimidine

HRID 919183Notes

Reaction equation

HRID 919183 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=O)=[CH:4][CH:3]=1.Cl.[C:19]([NH2:27])(=[NH:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[OH-].[Na+]>C(O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=3)[N:27]=[C:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[N:26]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 80289Benzamidine, hydrochlorideHCID 11833055HCID 11833055, compound

Product 1

HCID 600480204-(4-Bromophenyl)-2-phenyl-6-(pyridin-2-yl)pyrimidineYield 25%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 160 mL of an ethanol solution of 13.0 g (45.1 mmol) of (E)-3-(4-bromophenyl)-1-(2-pyridyl)-2-propen-1-one, 7.3 g (46.6 mmol) of benzamidine hydrochloride and 3.6 g (90 mmol) of sodium hydroxide were added under argon atmosphere, and the mixture was stirred for 16 h under heat refluxing. After cooling the reaction mixture to room temperature, a formed solid was collected by filtration and washed with water and methanol to obtain 4.31 g (yield: 25%) of 4-(4-bromophenyl)-2-phenyl-6-(2-pyridyl)pyrimidine as a pale brown solid.

Workup

  1. temperatureunder heat
  2. temperaturerefluxing
  3. filtrationa formed solid was collected by filtration
  4. washwashed with water and methanol

Sources & evidence

ORD record
ord-ff5e00cf817c4ab98c9e6a7a73fc4228
Source dataset
uspto-grants-2016_03
Patent number
US09273002B2

Reaction notes

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