2-Aminopyrimidine → HCID 21486767, compound

HRID 1414214Notes

Reaction equation

HRID 1414214 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([S:8][CH3:9])[CH:5]=[CH:4][C:3]=1[CH2:10][CH2:11][CH2:12]Br.[NH2:14][C:15]1[N:20]=[CH:19][CH:18]=[CH:17][N:16]=1>C1(C)C(C)=CC=CC=1>[Br-:1].[NH2:14][C:15]1[N:20]=[CH:19][CH:18]=[CH:17][N+:16]=1[CH2:12][CH2:11][CH2:10][C:3]1[CH:4]=[CH:5][C:6]([S:8][CH3:9])=[CH:7][C:2]=1[Br:1]

Participants

4

Reactant 2

HCID 79782-AminopyrimidineHCID 21486763HCID 21486763, compound

Product 1

HCID 21486767HCID 21486767, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

Procedure

To a solution of 154.0 g of 3-(2-bromo-4-methylthiophenyl)propyl bromide in 400 ml of dry xylene, is added a solution of 70.0 g of 2-aminopyrimidine in 300 ml of dry xylene and the mixture is heated under reflux for about 18 hours. The cooled xylene solution is decanted from the crystalline solid, the solid is triturated with 200 ml of 2-propanol and filtered to give 117.0 g of crude product. Recrystallization of the latter from 2-propanol gives about 98.0 g of 2-amino-1-[3-(2-bromo-4-methylthiophenyl)propyl]-pyrimidinium bromide.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for about 18 hours
  3. customThe cooled xylene solution is decanted from the crystalline solid
  4. customthe solid is triturated with 200 ml of 2-propanol
  5. filtrationfiltered
  6. customto give 117.0 g of crude product
  7. customRecrystallization of the latter from 2-propanol

Sources & evidence

ORD record
ord-dfc6ee9d21b641699a5f30b06e452780
Source dataset
uspto-grants-1977_01
Patent number
US04001233

Reaction notes

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