Sodium Methoxide → 2(1H)-Pyrimidinimine, 1-[2-(2-bromophenyl)ethyl]-

HRID 1076571Notes

Reaction equation

HRID 1076571 reaction equation
C[O-].[Na+].[Br-].[NH2:5][C:6]1[N:11]=[CH:10][CH:9]=[CH:8][N+:7]=1[CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[Br:20]>CO>[NH:5]=[C:6]1[N:11]=[CH:10][CH:9]=[CH:8][N:7]1[CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[Br:20]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 12255218HCID 12255218, compound

Product 1

HCID 122552202(1H)-Pyrimidinimine, 1-[2-(2-bromophenyl)ethyl]-Yield 81.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3.3 g of sodium methoxide in 120 ml of anhydrous methanol is added 10.8 g of 2-amino-1-(o-bromophenethyl)pyrimidinium bromide, prepared as described in example 1 (G). The solution is stirred under nitrogen for 2 hours and then heated under reflux for 5 hours. The solvent is removed in vacuo and the residue is treated with 200 ml of anhydrous ether. The ether solution is washed, dried, and concentrated in vacuo to give about 6.8 g of yellow solid. This is recrystallized from hexane to give the name product, mp about 97°-98°.

Workup

  1. customprepared
  2. temperatureheated
  3. temperatureunder reflux for 5 hours
  4. customThe solvent is removed in vacuo
  5. additionthe residue is treated with 200 ml of anhydrous ether
  6. washThe ether solution is washed
  7. customdried
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2348518e06264c46885f8a96105fd126
Source dataset
uspto-grants-1976_05
Patent number
US03957787

Reaction notes

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