Chlorosuccinimide → 5,6-Dichloro-2,4-pyrimidinediamine

HRID 128926Notes

Reaction equation

HRID 128926 reaction equation
[Cl:1]N1C(=O)CCC1=O.[NH2:9][C:10]1[N:15]=[C:14]([NH2:16])[CH:13]=[C:12]([Cl:17])[N:11]=1>CO.O>[NH2:9][C:10]1[N:15]=[C:14]([NH2:16])[C:13]([Cl:1])=[C:12]([Cl:17])[N:11]=1

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 674322,4-Diamino-6-chloropyrimidine

Product 1

HCID 3456315,6-Dichloro-2,4-pyrimidinediamineYield 79.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

50 g of N-chlorosuccinimide are added in portions at 23° C. to a solution of 45 g of 2,4-diamino-6-chloropyrimidine in methanol (1030 ml). On completion of addition, the reaction mixture is stirred at room temperature for 3 hours. The methanol is evaporated under reduced pressure and the crude product obtained is taken up under reflux in 850 ml of water for 1 hour. After filtering, the crude product is recrystallized two times from an EtOH:H2O (80:20) mixture to give 44.5 g of 2,4-diamino-5,6-dichloropyrimidine.

Workup

  1. additionOn completion of addition
  2. customThe methanol is evaporated under reduced pressure
  3. customthe crude product obtained
  4. filtrationAfter filtering
  5. customthe crude product is recrystallized two times from an EtOH:H2O (80:20) mixture

Sources & evidence

ORD record
ord-e06e5c1bfcbe407faaf88f8e3532dfcd
Source dataset
uspto-grants-1995_11
Patent number
US05466694

Reaction notes

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