Dichloromethane → 5-Chloro-2-(methylsulfonyl)-7-morpholinothiazolo[4,5-d]pyrimidine

HRID 1692804Notes

Reaction equation

HRID 1692804 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:5]2[S:10][C:9](SC)=[N:8][C:6]=2[N:7]=1.O[O:20][S:21]([O-:23])=O.[K+].[CH2:25](Cl)Cl>CO.O>[Cl:1][C:2]1[N:3]=[C:4]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:5]2[S:10][C:9]([S:21]([CH3:25])(=[O:23])=[O:20])=[N:8][C:6]=2[N:7]=1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 23707502Potassium hydroxy sulfite2×HCID 57685391HCID 57685391, compound

Product 1

HCID 576854065-Chloro-2-(methylsulfonyl)-7-morpholinothiazolo[4,5-d]pyrimidine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

5-Chloro-2-(methylthio)-7-morpholinothiazolo[4,5-d]pyrimidine was dissolved in methanol. Oxone (2.2 eq) was added in water (10:1 ratio methanol:water). The solution was heated to 50° C. for 2.5 hours. One additional equivalent of oxone was added (if needed) and solution was stirred at 50° C. for an additional 1 hour. The solution was cooled to room temperature and methylene chloride was added. The resulting solid was filtered off and rinsed with methylene chloride. The organic solution was washed with saturated sodium bicarbonate solution (pH test neutral), dried with magnesium sulfate and concentrated to yield 5-chloro-2-(methylsulfonyl)-7-morpholinothiazolo[4,5-d]pyrimidine.

Workup

  1. temperatureThe solution was cooled to room temperature
  2. filtrationThe resulting solid was filtered off
  3. washrinsed with methylene chloride
  4. washThe organic solution was washed with saturated sodium bicarbonate solution (pH test neutral),
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0ea378599fb047a3bc9e9dfa5c29fc39
Source dataset
uspto-grants-2012_04
Patent number
US08158626B2

Reaction notes

Loading…