2-Methylbenzenesulfonic acid → HCID 18366600, compound

HRID 379590Notes

Reaction equation

HRID 379590 reaction equation
O1CCCCC1[O:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[C:20]2[C:19](=[O:21])[N:18]([CH3:22])[C:17](=[O:23])[N:16]([CH2:24][CH:25]([CH3:27])[CH3:26])[C:15]=2[S:14][C:13]=1[CH2:28][C:29]1[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=1.C1(C)C(S(O)(=O)=O)=CC=CC=1>CO>[OH:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[C:20]2[C:19](=[O:21])[N:18]([CH3:22])[C:17](=[O:23])[N:16]([CH2:24][CH:25]([CH3:27])[CH3:26])[C:15]=2[S:14][C:13]=1[CH2:28][C:29]1[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=1

Participants

4

Reactant 2

HCID 69252-Methylbenzenesulfonic acidHCID 18366583HCID 18366583, compound

Product 1

HCID 18366600HCID 18366600, compoundYield 21.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-{3-[(tetrahydro-2H-pyran-2-yl)oxy]propoxy}-3-methyl-1-(2-methylpropyl)-6-[(3-pyridinyl)methyl]thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (230 mg) was dissolved in methanol (3 ml). Toluenesulfonic acid (190 mg) was added and the mixture was stirred for 5 h. The methanol was evaporated, sodium bicarbonate (aqueous) and ethyl acetate were added and the phases were separated. The aqueous phase was extracted twice with ethyl acetate, the ethyl acetate layers were combined, washed with brine, dried, filtered and evaporated. The residue was purified by chromatography (ethyl acetate) and HPLC (dichloromethane:ethanol 100-90:0-10) then dissolved in aqueous ethanol and precipitated by addition of water to give the title compound (41 mg).

Workup

  1. customThe methanol was evaporated
  2. additionsodium bicarbonate (aqueous) and ethyl acetate were added
  3. customthe phases were separated
  4. extractionThe aqueous phase was extracted twice with ethyl acetate
  5. washwashed with brine
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by chromatography (ethyl acetate) and HPLC (dichloromethane:ethanol 100-90:0-10)
  10. dissolutionthen dissolved in aqueous ethanol
  11. customprecipitated by addition of water

Sources & evidence

ORD record
ord-d98ffcd0a1aa4bb0a337b519f2fade94
Source dataset
uspto-grants-2001_10
Patent number
US06300334B1

Reaction notes

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