Sodium ethoxide → 2-(4-Bromobenzyl)-4-(4-bromophenyl)pyrimidine

HRID 1779334Notes

Reaction equation

HRID 1779334 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH2:11])=[NH:10])=[CH:4][CH:3]=1.[O-][CH2:13][CH3:14].[Na+]>C(O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]2[N:11]=[C:8]([C:14]3[CH:13]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=3)[CH:5]=[CH:6][N:10]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 2723922Sodium ethoxide2×HCID 502071359104-21-1

Product 1

HCID 214764092-(4-Bromobenzyl)-4-(4-bromophenyl)pyrimidineYield 154.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred mixture of 4-bromophenylacetamidine (11.25 g, 0.04 mole) and 1-dimethylamino-3-dimethylimonio-1-(4-bromophenyl)-1-propane perchlorate (15.25 g, 0.04 mole) in 100 mL of dry ethanol is added 0.04 mole sodium ethoxide (prepared from 0.92 g Na and 65 mL ethanol). After stirring for 30 min at room temperature a further equivalent of sodium ethoxide is added, and the mixture is heated under reflux for 2 hr. The solvent is removed under reduced pressure, and the yellow-brown residue triturated with 150 mL water. The solid is filtered, washed with water, dried in air and recrystallized from ether:hexane (1:3) to give 12.5 g (77%) of a pale yellow crystalline solid, mp 93°-94° C.

Workup

  1. additionis added
  2. temperaturethe mixture is heated
  3. temperatureunder reflux for 2 hr
  4. customThe solvent is removed under reduced pressure
  5. customthe yellow-brown residue triturated with 150 mL water
  6. filtrationThe solid is filtered
  7. washwashed with water
  8. customdried in air
  9. customrecrystallized from ether:hexane (1:3)

Sources & evidence

ORD record
ord-5071f790800c4eb399065672a30b6e4f
Source dataset
uspto-grants-1997_05
Patent number
US05627184

Reaction notes

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