Methanol → HCID 178503559, compound

HRID 2050003Notes

Reaction equation

HRID 2050003 reaction equation
[NH:1]1[C:8](=[O:9])[CH2:7][C:5](=[O:6])[NH:4][C:2]1=[S:3].[CH3:10]O.[OH-].[Na+].CI>O>[CH3:10][S:3][C:2]1[N:4]=[C:5]([OH:6])[CH:7]=[C:8]([OH:9])[N:1]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 2723628Thiobarbituric acid

Product 1

HCID 178503559HCID 178503559, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
41 °C

Procedure

A quantity (72.07 g., 0.5 mole) of 2-thiobarbituric acid was dissolved in a reaction medium consisting of 500 ml. methanol, 500 ml. water, and 20 g. sodium hydroxide. The medium was heated in order to effect solution. After cooling the solution to 41° C., 142 g. (1.0 mole) methyl iodide was added, with stirring. The reaction mixture was heated at the reflux temperature for 1 hr. The desired 2-(methylthio)-4,6-pyrimidinediol crystallized out as the refluxing continued, and it was recovered on a filter by cooling the reaction mixture to 60° C. and filtering. The initial crop of crystalline product weighed 51.5 g. and had a melting point at >300° C. After refrigerating the mother liquor, an additional 19.08 g. of product was obtained.

Workup

  1. temperatureThe medium was heated in order
  2. temperatureThe reaction mixture was heated at the reflux temperature for 1 hr
  3. customThe desired 2-(methylthio)-4,6-pyrimidinediol crystallized out as the refluxing
  4. customit was recovered on
  5. filtrationa filter
  6. temperatureby cooling the reaction mixture to 60° C.
  7. filtrationfiltering
  8. customat >300° C
  9. customof product was obtained

Sources & evidence

ORD record
ord-08c5a66725ec4dcea7b9cae639998754
Source dataset
uspto-grants-1980_04
Patent number
US04199583

Reaction notes

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