Formaldehyde → 4,6-Dimethyl-2-(morpholin-4-ylthiocarbonylthiomethylamino)pyrimidine

HRID 2165741Notes

Reaction equation

HRID 2165741 reaction equation
[OH-].[K+].[NH:3]1[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.[C:9](=[S:11])=[S:10].C=O.[NH2:14][C:15]1[N:20]=[C:19]([CH3:21])[CH:18]=[C:17]([CH3:22])[N:16]=1.[CH3:23]S(O)(=O)=O>O>[CH3:22][C:17]1[CH:18]=[C:19]([CH3:21])[N:20]=[C:15]([NH:14][CH2:23][S:10][C:9]([N:3]2[CH2:8][CH2:7][O:6][CH2:5][CH2:4]2)=[S:11])[N:16]=1

Participants

8

Reactant 6

HCID 712FormaldehydeHCID 6348Carbon DisulfideHCID 6395Methanesulfonic AcidHCID 8083MorpholineHCID 130212-Amino-4,6-dimethyl pyrimidineHCID 14797Potassium Hydroxide

Product 1

HCID 539986464,6-Dimethyl-2-(morpholin-4-ylthiocarbonylthiomethylamino)pyrimidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

6.6 g (0.1 mole) of 85% potassium hydroxide and 8.9 g (0.1 mole) of morpholine are dissolved in 200 ml of water and, with cooling, 7.7 g (0.1 mole) of carbon disulfide are added. The mixture is stirred until a yellowish homogeneous solution is obtained. With cooling and stirring, 9.4 g (0.11 mole) of aqueous 35% formaldehyde and a solution of 12.7 g (0.1 mole) of 2-amino-4,6-dimethylpyrimidine and 9.7 g (0.1 mole) of methanesulfonic acid in 50 ml of water are added in succession. The reaction mixture is further stirred at room temperature, whereupon first an oil precipitates, which crystallises after a short time. After 24 hours the batch is diluted with 1 liter of water and the crystalline precipitate is filtered with suction and dried, affording 24 g (80% of theory) of the title compound with a melting point of 119°-121° C.

Workup

  1. temperaturewith cooling
  2. customis obtained
  3. temperatureWith cooling
  4. stirringstirring
  5. stirringThe reaction mixture is further stirred at room temperature
  6. customwhereupon first an oil precipitates
  7. customwhich crystallises after a short time
  8. additionAfter 24 hours the batch is diluted with 1 liter of water
  9. filtrationthe crystalline precipitate is filtered with suction
  10. customdried

Sources & evidence

ORD record
ord-bf3f2026785241afa0de28d55ec329c2
Source dataset
uspto-grants-1990_07
Patent number
US04940792

Reaction notes

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