Dimethyl Sulfide → HCID 73016309, compound

HRID 2038193Notes

Reaction equation

HRID 2038193 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.[C:31](=[O:34])([O-])[O-].[K+].[K+].C(=O)(O)[O-].[Na+]>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([CH:14]=[CH:15][CH:31]=[O:34])=[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

6

Reactant 4

HCID 1068Dimethyl SulfideHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 54765061HCID 54765061, compound

Product 1

HCID 73016309HCID 73016309, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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 through 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. To the reaction mixture, potassium carbonate (2.8 g, 20.3 mmol) is added at room temperature. The progress of the reaction is monitored by TLC. Upon completion of the reaction, 150 ml sodium bicarbonate (aq.) is added and methanol is distilled off under reduced pressure. The residue is extracted with ethyl acetate (2×300 mL) and washed with DM water (100 mL) and brine (150 mL). The organic solvent is distilled off under reduced pressure to give 3.7 g (95%) of N-(4-(4-fluorophenyl)-6-isopropyl-5-(3-oxoprop-1-enyl)pyrimidin-2-yl)-N-methyl-methanesulfonamide The product is recrystallized from 20% ethylacetate:cyclohexane at 0° C. to 5° C. to afford 2.4 g (67%) of N-(4-(4-fluorophenyl)-6-isopropyl-5-(3-oxoprop-1-enyl)pyrimidin-2-yl)-N-methyl-methanesulfonamide as an oily white-yellow solid.

Workup

  1. customO3 gas is bubbled through the solution at −15° C. to −10° C. for 60 min
  2. customReaction solution
  3. customis bubbled through with Argon for 2 min
  4. customto remove the excess of O3
  5. temperaturemaintaining
  6. additionis added
  7. distillationmethanol is distilled off under reduced pressure
  8. extractionThe residue is extracted with ethyl acetate (2×300 mL)
  9. washwashed with DM water (100 mL) and brine (150 mL)
  10. distillationThe organic solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-6af4e93708844720a94b98ce21aa774c
Source dataset
uspto-grants-2013_11
Patent number
US08575343B2

Reaction notes

Loading…