Sodium ethoxide → 5-Methyl-2,4-bis(4-bromophenyl)pyrimidine

HRID 54224Notes

Reaction equation

HRID 54224 reaction equation
[O-][CH2:2]C.[Na+].[Na].C1(S(O)(=O)=O)C=CC=CC=1.[Br:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]([NH2:23])=[NH:22])=[CH:19][CH:18]=1.CN(C)C=[C:29](C)[C:30]([C:32](=O)[C:33]1[CH:38]=[CH:37][C:36]([Br:39])=[CH:35][CH:34]=1)=O>C(O)C>[CH3:2][C:30]1[C:32]([C:33]2[CH:34]=[CH:35][C:36]([Br:39])=[CH:37][CH:38]=2)=[N:22][C:21]([C:20]2[CH:24]=[CH:25][C:17]([Br:16])=[CH:18][CH:19]=2)=[N:23][CH:29]=1

Participants

6

Reactant 4

HCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 21476408p-Bromobenzamidine benzenesulfonateHCID 54209384HCID 54209384, compound

Product 1

HCID 107161785-Methyl-2,4-bis(4-bromophenyl)pyrimidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Sodium ethoxide (0.06 mole), (prepared from 1.38 g sodium in 75 mL absolute ethanol) is gradually added to a stirred suspension of p-bromobenzamidine benzenesulfonate (10.7 g, 0.03 mole), and 3-dimethylamino-1-(4-bromobenzoyl)-2-methylpropen-1-one (8.04 g, 0.03 mole) in 75 mL absolute ethanol, and the reaction mixture is heated under reflux for 12-16 hr (TLC monitored). Solvent is distilled and the residue is treated with 150 mL water. The resulting solid is filtered, washed with water and dried. The product is dissolved in 250 mL chloroform, dried over anhydrous sodium sulfate, filtered, concentrated and recrystallized from chloroform:ether (1:4) to yield 7.75 g (64%) of a white crystallized solid, mp 136°-137° C.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureunder reflux for 12-16 hr (TLC monitored)
  3. distillationSolvent is distilled
  4. additionthe residue is treated with 150 mL water
  5. filtrationThe resulting solid is filtered
  6. washwashed with water
  7. customdried
  8. dissolutionThe product is dissolved in 250 mL chloroform
  9. dry with materialdried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customrecrystallized from chloroform:ether (1:4)
  13. customto yield 7.75 g (64%) of
  14. customa white crystallized solid, mp 136°-137° C.

Sources & evidence

ORD record
ord-15428d1ad2594809870a0f8d4cbd6538
Source dataset
uspto-grants-1997_04
Patent number
US05622955

Reaction notes

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