Dimethyl Sulfoxide → HCID 178493554, compound

HRID 2372658Notes

Reaction equation

HRID 2372658 reaction equation
[CH3:1][C:2]([O-:5])(C)[CH3:3].[K+].[C:7]1([C:13]2[CH:14]=[CH:15][CH:16]=[C:17](S)[C:18]=2C(O)=O)[CH:12]=[CH:11]C=CC=1.[CH3:23][O:24][C:25]1[CH:30]=[C:29]([O:31][CH3:32])[N:28]=[C:27](S(C)(=O)=O)[N:26]=1.P(=O)(O)(O)[OH:38].C[S:43]([CH3:45])=O>CCOCC.O>[CH3:32][O:31][C:29]1[CH:30]=[C:25]([O:24][CH3:23])[N:26]=[C:27]([O:5][C:2]2[CH:3]=[CH:11][CH:12]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:1]=2[C:45]([OH:38])=[S:43])[N:28]=1

Participants

8

Reactant 5

HCID 679Dimethyl SulfoxideHCID 1004Phosphoric AcidHCID 8383634,6-Dimethoxy-2-(methylsulfonyl)pyrimidineHCID 19823894HCID 19823894, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 178493554HCID 178493554, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
35 °C

Procedure

0.55 g (4.9 mmol) of potassium tert-butylate is added a little at a time to a solution of 0.6 g (2.4 mmol) of 6-phenylthiosalicylic acid in 8 ml of dimethyl sulfoxide, the temperature increasing to 35° C. The mixture is cooled to room temperature, after which 0.53 g (2.4 mmol) of 4,6-dimethoxy-2-methylsulfonylpyrimidine is added and stirring is carried out for one hour at room temperature. The content of the flask is poured onto a mixture of 100 ml of cold water, 1 ml of orthophosphoric acid and 50 ml of ether. The ether phase is washed with 5% strength phosphoric acid and water, dried and evaporated down. After the crude product has been stirred with cold toluene, 0.50 g (54%) of the above product of melting point 135°-136° C. is isolated.

Workup

  1. temperatureThe mixture is cooled to room temperature
  2. washThe ether phase is washed with 5% strength phosphoric acid and water
  3. customdried
  4. customevaporated down
  5. stirringAfter the crude product has been stirred with cold toluene, 0.50 g (54%) of the above product of melting point 135°-136° C.
  6. customis isolated

Sources & evidence

ORD record
ord-7298047da7d2498b95b81b12fd3db452
Source dataset
uspto-grants-1992_03
Patent number
US05100458

Reaction notes

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