Methanol → HCID 73016309, compound

HRID 2038192Notes

Reaction equation

HRID 2038192 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([CH:14](O)[CH2:15]C=C)=[C:12]([CH:19]([CH3:21])[CH3:20])[N:11]=[C:10]([N:22]([CH3:27])[S:23]([CH3:26])(=[O:25])=[O:24])[N:9]=2)=[CH:4][CH:3]=1.CSC.[CH3:31][OH:32]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([CH:14]=[CH:15][CH:31]=[O:32])=[C:12]([CH:19]([CH3:21])[CH3:20])[N:11]=[C:10]([N:22]([CH3:27])[S:23]([CH3:26])(=[O:25])=[O:24])[N:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1068Dimethyl SulfideHCID 54765061HCID 54765061, compound

Product 1

HCID 73016309HCID 73016309, compound

Procedure

N-[4-(4-fluorophenyl)-5-(1-hydroxybut-3-enyl)-6-isopropyl-pyrimidin-2-yl]-N-methylmethanesulfonamide (4 g, 10.2 mmol) is diluted in 102 mL methanol. O3 gas is bubbled through the solution at −15° C. to −10° C. for 60 min. Reaction solution is bubbled with Argon for 2 min to remove the excess of O3. Dimethylsulfide (1.5 ml, 20.3 mmol) is added to the solution, maintaining stirring for 2 hours. Upon completion of the reaction, the solution is distilled under reduced pressure to remove the excess of dimethylsulfide and solvent. The residue is diluted in 200 mL dichloromethane, washed with DM water (50 mL), brine (50 mL) and dried over magnesium sulfate (1 g). The solvent is removed by distillation under reduced pressure to afford 4.1 g of N-[4-(4-fluorophenyl)-6-isopropyl-5-(3-oxoprop-1-enyl)pyrimidin-2-yl]-N-methylmethanesulfonamide.

Workup

  1. customO3 gas is bubbled through the solution at −15° C. to −10° C. for 60 min
  2. customReaction solution
  3. customis bubbled with Argon for 2 min
  4. customto remove the excess of O3
  5. temperaturemaintaining
  6. customUpon completion of the reaction
  7. distillationthe solution is distilled under reduced pressure
  8. customto remove the excess of dimethylsulfide and solvent
  9. additionThe residue is diluted in 200 mL dichloromethane
  10. washwashed with DM water (50 mL), brine (50 mL)
  11. dry with materialdried over magnesium sulfate (1 g)
  12. customThe solvent is removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-94d10aaafe2c4e19aa59095ffb3ba45a
Source dataset
uspto-grants-2013_11
Patent number
US08575343B2

Reaction notes

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