Water → 2-(ethylthio)-5-(2-hydroxy-ethyl)-3,6-dimethyl-4(3H)-pyrimidinone

HRID 580893Notes

Reaction equation

HRID 580893 reaction equation
[OH-].[K+].[CH2:3]([S:5][C:6]1[NH:11][C:10](=[O:12])[C:9]([CH2:13][CH2:14][OH:15])=[C:8]([CH3:16])[N:7]=1)[CH3:4].I[CH3:18].O>CS(C)=O>[CH2:3]([S:5][C:6]1[N:11]([CH3:18])[C:10](=[O:12])[C:9]([CH2:13][CH2:14][OH:15])=[C:8]([CH3:16])[N:7]=1)[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 1361744192-(ethylthio)-5-(2-hydroxyethyl)-6-methyl-4(3H)-pyrimidinone

Product 1

HCID 539107212-(ethylthio)-5-(2-hydroxy-ethyl)-3,6-dimethyl-4(3H)-pyrimidinoneYield 46.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
65 °C

Procedure

Potassium hydroxide (8.4 g) was added to a solution of intermediate 2 (33 g) in dimethyl sulfoxide (150 ml). The mixture was stirred for 1 hour at 60-70 ° C. The mixture was cooled to 20° C. and iodomethane (21.3 g) was added dropwise. The reaction mixture was stirred overnight at RT. The mixture was poured out into water and extracted with toluene. The separated organic layer was dried, filtered and the solvent was evaporated. The residue was crystallized from 4-methyl-2-pentanone and the precipitate was filtered off and dried, yielding 16 g (46%) of 2-(ethylthio)-5-(2-hydroxy-ethyl)-3,6-dimethyl-4(3H)-pyrimidinone (intermediate 3).

Workup

  1. temperatureThe mixture was cooled to 20° C.
  2. stirringThe reaction mixture was stirred overnight at RT
  3. extractionextracted with toluene
  4. customThe separated organic layer was dried
  5. filtrationfiltered
  6. customthe solvent was evaporated
  7. customThe residue was crystallized from 4-methyl-2-pentanone
  8. filtrationthe precipitate was filtered off
  9. customdried

Sources & evidence

ORD record
ord-f6b2e27c89a74c049300426e677dc6d6
Source dataset
uspto-grants-1999_07
Patent number
US05919788

Reaction notes

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