Methanol → HCID 19781614, compound

HRID 257794Notes

Reaction equation

HRID 257794 reaction equation
CS[C:3]1[CH:4]=[C:5]([N:9]2[C:14]3[N:15]=[CH:16][CH:17]=[CH:18][C:13]=3[C:12](=[O:19])[N:11]([CH2:20][C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)[C:10]2=[O:27])[CH:6]=[CH:7][CH:8]=1.[OH:28][S:29]([O-:32])(=O)=O.[K+].OOS([O-])=O.[K+].[CH3:40]O>O>[CH3:40][S:29]([C:7]1[CH:6]=[C:5]([N:9]2[C:14]3[N:15]=[CH:16][CH:17]=[CH:18][C:13]=3[C:12](=[O:19])[N:11]([CH2:20][C:21]3[CH:22]=[CH:23][N:24]=[CH:25][CH:26]=3)[C:10]2=[O:27])[CH:4]=[CH:3][CH:8]=1)(=[O:32])=[O:28]

Participants

6

Reactant 4

HCID 887MethanolHCID 516920Potassium bisulfateHCID 19781593HCID 19781593, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 19781614HCID 19781614, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

1-(3-Methylthiophenyl)-3-(4-pyridylmethyl)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (250 mg, 0.664 mmole), prepared, e.g., as described in Example 5B, was dissolved in methanol (3 ml) and cooled to 0° C. To this solution, a 50% solution of 2KHSO5. KHSO4.K2SO4 in H2O, (this reagent is commercially available under the trademark of "OXONE®" from the Aldrich Chemical Company), (1.22 g, 1.99 mmole) was added. A cloudy slurry was formed and stirred at room temperature for 4 hours. The reaction mixture was diluted by adding H2O (2.4 ml) and extracted three times with methylene chloride (3×5 ml). The organic phases were combined and dried over Na2SO4, followed by filtration. The solvent was removed and the residue was dissolved in ethyl acetate/ethyl ether. The product was recrystallized out of the solution yielding 190 mg (0.465 mmole, 79% yield) of 1-(3-methylsulfonylphenyl)-3-(4-pyridylmethyl)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (mp 254°-256° C.) as a white solid.

Workup

  1. additionwas added
  2. customA cloudy slurry was formed
  3. additionThe reaction mixture was diluted
  4. extractionextracted three times with methylene chloride (3×5 ml)
  5. dry with materialdried over Na2SO4
  6. filtrationfollowed by filtration
  7. customThe solvent was removed
  8. dissolutionthe residue was dissolved in ethyl acetate/ethyl ether
  9. customThe product was recrystallized out of the solution

Sources & evidence

ORD record
ord-35d132eba9204093bd0b1905ab6235c9
Source dataset
uspto-grants-1993_11
Patent number
US05264437

Reaction notes

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