Dimethyl Sulfoxide → HCID 67196613, compound

HRID 550801Notes

Reaction equation

HRID 550801 reaction equation
[O:1]=[S:2]1(=[O:28])[CH2:10][C:9]2[C:8]([N:11]3[CH2:17][CH2:16][C:15](=[O:18])[NH:14][CH2:13][CH2:12]3)=[N:7][C:6]([C:19]3[CH:24]=[C:23]([F:25])[C:22](F)=[CH:21][C:20]=3[F:27])=[N:5][C:4]=2[CH2:3]1.[CH3:29][S:30](C)=O.C[S-].[Na+]>O>[F:27][C:20]1[CH:21]=[C:22]([S:30][CH3:29])[C:23]([F:25])=[CH:24][C:19]=1[C:6]1[N:7]=[C:8]([N:11]2[CH2:17][CH2:16][C:15](=[O:18])[NH:14][CH2:13][CH2:12]2)[C:9]2[CH2:10][S:2](=[O:28])(=[O:1])[CH2:3][C:4]=2[N:5]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 4378561Sodium methanethiolate2×HCID 67199410HCID 67199410, compound

Product 1

HCID 67196613HCID 67196613, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 500 mg of 1-[6,6-dioxido-2-(2,4,5-trifluorophenyl)-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl]-1,4-diazepan-5-one and 5 ml of DMSO, 89 mg of sodium thiomethoxide was added, the mixture was stirred at ambient temperature for 1 hour, here was then added 21 mg of sodium thiomethoxide, and the mixture was stirred at ambient temperature for 30 minutes. To the reaction mixture was added 50 ml of water, and the precipitate was collected by filtration, washed with water, and dried under reduced pressure. The filtrate was separately extracted with a mixture of EtOAc and THF, the organic phase obtained was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the solid obtained was combined with the former solid. The mixture was purified by silica-gel column chromatography (chloroform-MeOH) to yield 352 mg of 1-{2-[2,5-difluoro-4-(methylthio)phenyl]-6,6-dioxido-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl}-1,4-diazepan-5-one.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred at ambient temperature for 30 minutes
  3. filtrationthe precipitate was collected by filtration
  4. washwashed with water
  5. customdried under reduced pressure
  6. extractionThe filtrate was separately extracted with a mixture of EtOAc and THF
  7. customthe organic phase obtained
  8. dry with materialwas dried over anhydrous magnesium sulfate
  9. distillationthe solvent was distilled off under reduced pressure
  10. customthe solid obtained
  11. customThe mixture was purified by silica-gel column chromatography (chloroform-MeOH)

Sources & evidence

ORD record
ord-41f3a484cafb46b1b5d674e132fe5b48
Source dataset
uspto-grants-2011_05
Patent number
US07947690B2

Reaction notes

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