5-Amino-2,4-dichloropyrimidine → 5-Amino-2-chloro-4-methylthiopyrimidine

HRID 343379Notes

Reaction equation

HRID 343379 reaction equation
[CH3:1][S-:2].[Na+].[NH2:4][C:5]1[C:6](Cl)=[N:7][C:8]([Cl:11])=[N:9][CH:10]=1>CO>[NH2:4][C:5]1[C:6]([S:2][CH3:1])=[N:7][C:8]([Cl:11])=[N:9][CH:10]=1

Participants

4

Reactant 2

HCID 2577975-Amino-2,4-dichloropyrimidineHCID 4378561Sodium methanethiolate

Product 1

HCID 187048095-Amino-2-chloro-4-methylthiopyrimidineYield 35%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium methanethiolate (0.342 g) was added to a solution of 5-amino-2,4-dichloropyrimidine (1 g) in methanol (5 ml) and the mixture was heated at reflux for 2 hours. Volatile material was then removed by evaporation and water (1 ml) was added. The suspended solid was collected by filtration, washed with hexane (10 ml) and dried under vacuum to give 5-amino-2-chloro-4-methylthiopyrimidine (0.3 g); 1H NMR (CDCl3): 2.55 (s, 3H), 7.75 (s, 1H); mass spectrum (+ve CI): 175 (M+H)+.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 2 hours
  3. customVolatile material was then removed by evaporation and water (1 ml)
  4. additionwas added
  5. filtrationThe suspended solid was collected by filtration
  6. washwashed with hexane (10 ml)
  7. customdried under vacuum

Sources & evidence

ORD record
ord-de8bf311c65c46e2a5e7d32fa106cf0d
Source dataset
uspto-grants-1999_01
Patent number
US05861401

Reaction notes

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