Water → HCID 13961960, compound

HRID 2309105Notes

Reaction equation

HRID 2309105 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([OH:8])[N:5]=[C:4]([S:9][CH3:10])[N:3]=1.O.O1CCOCC1.Cl[CH:19]([F:21])[F:20]>[OH-].[K+].C1OCCOCCOCCOCCOCCOC1>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH:19]([F:21])[F:20])[N:5]=[C:4]([S:9][CH3:10])[N:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6372ChlorodifluoromethaneHCID 312751,4-DioxaneHCID 178503550HCID 178503550, compound

Product 1

HCID 13961960HCID 13961960, compoundYield 84.6%

Reagents, catalysts & solvents 2

HCID 2855718-Crown-6CatalystHCID 14797Potassium HydroxideSolvent

Conditions

Temperature
40 °C

Procedure

6.8 g (0.036 mole) of 4-chloro-6-hydroxy-2-methylthiopyrimidine are suspended in 25 ml 50% potassium hydroxide solution, 25 ml of water and 100 ml of dioxane. After the addition of 0.5 g of 18-crown-6, the reaction mixture is heated to 40° C., and 10 g of chlorodifluoromethane are subsequently introduced over 3 hours. The mixture is then cooled to room temperature, the phases are separated and the organic phase is evaporated to dryness. The residue is crystallised from methanol/water, affording 6.9 g (84.4% of theory) of 4-chloro-6-difluoromethoxy-2-methylthiopyrimidine with a melting point of 36°-37° C. The substance has a boiling point of 76°-78° C. at 0.15 mbar.

Workup

  1. temperatureThe mixture is then cooled to room temperature
  2. customthe phases are separated
  3. customthe organic phase is evaporated to dryness
  4. customThe residue is crystallised from methanol/water

Sources & evidence

ORD record
ord-60f65ae7f79d48c8b930d75771cf994d
Source dataset
uspto-grants-1987_09
Patent number
US04692524

Reaction notes

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