Sodium Methoxide → 2-Amino-4-methoxy-6-(pyridin-2-ylthiomethyl)pyrimidine

HRID 980768Notes

Reaction equation

HRID 980768 reaction equation
C[O-].[Na+].[SH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=1.[NH2:11][C:12]1[N:17]=[C:16]([CH2:18]Cl)[CH:15]=[C:14]([O:20][CH3:21])[N:13]=1>CO.O>[NH2:11][C:12]1[N:13]=[C:14]([O:20][CH3:21])[CH:15]=[C:16]([CH2:18][S:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=2)[N:17]=1

Participants

6

Reactant 3

HCID 10942334Sodium MethoxideHCID 138848154-(Chloromethyl)-6-methoxypyrimidin-2-amineHCID 178418616HCID 178418616, compound

Product 1

HCID 200708422-Amino-4-methoxy-6-(pyridin-2-ylthiomethyl)pyrimidine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

18 g of 30% methanolic sodium methylate solution are added to a solution of 11.1 g of 2-mercaptopyridine in 100 ml of methanol, and stirring is then maintained at 20°-25° C. for 1 hour. To this solution are added portionwise 17.4 g of 2-amino-4-chloromethyl-6-methoxy-pyrimidine, and the mixture is stirred at 20°-25° C. for a further 2 hours. In further processing, the mixture is diluted with 1 liter of water, and the precipitating crystalline product is separated and dried. The yield is 22.5 g (91% of theory) of 2-amino-4-methoxy-6-(pyridin-2-ylthiomethyl)-pyrimidine, m.p. 115°-116° C.

Workup

  1. temperatureis then maintained at 20°-25° C. for 1 hour
  2. stirringthe mixture is stirred at 20°-25° C. for a further 2 hours
  3. customthe precipitating crystalline product is separated
  4. customdried

Sources & evidence

ORD record
ord-9d98fc36d6b344c2b3c1d0e2c62c374c
Source dataset
uspto-grants-1987_01
Patent number
US04639264

Reaction notes

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