HCID 59420809, compound → HCID 178428221, compound

HRID 499069Notes

Reaction equation

HRID 499069 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([S:8]([CH3:11])(=O)=O)[N:5]=[C:4]([NH:12][C:13]2[NH:17][N:16]=[C:15]([CH3:18])[CH:14]=2)[CH:3]=1.[CH3:19][C:20]1[CH:29]=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=C(S)[CH:26]=2)[N:21]=1>C(O)(C)(C)C.C(OCC)(=O)C>[CH3:19][C:20]1[CH:29]=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[C:11]([S:8][C:6]3[N:5]=[C:4]([NH:12][C:13]4[NH:17][N:16]=[C:15]([CH3:18])[CH:14]=4)[CH:3]=[C:2]([Cl:1])[N:7]=3)[CH:26]=2)[N:21]=1

Participants

5

Reactant 2

HCID 59420809HCID 59420809, compoundHCID 178428229HCID 178428229, compound

Product 1

HCID 178428221HCID 178428221, compoundYield 19.1%

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred suspension of 6-chloro-N-(3-methyl-1H-pyrazol-5-yl)-2-(methylsulfonyl)pyrimidin-4-amine (2.02 g, 7.03 mmol) in tert-butanol (20 ml) was added 2-methylquinoline-6-thiol (1.23 g, 7.03 mmol). The mixture was heated to 70° C. for 4 hours, then cooled to ambient and diluted with ethyl acetate/saturated aqueous potassium carbonate. The mixture was filtered to remove unreacted starting material and the organic layer removed form the filtrate. The aqueous layer was extracted with ethyl acetate and the combined organic extracts washed with brine, dried (MgSO4), filtered and concentrated. The crude was purified on silica gel, eluting with 90 to 100% ethyl acetate/petrol. The title compound was further purified by trituration with dichloromethane. This gave the product as a white solid (514 mg, 19%); MS ES+ 383.25, ES− 381.36.

Workup

  1. temperaturecooled
  2. filtrationThe mixture was filtered
  3. customto remove unreacted
  4. customthe organic layer removed form the filtrate
  5. extractionThe aqueous layer was extracted with ethyl acetate
  6. washthe combined organic extracts washed with brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude was purified on silica gel
  11. washeluting with 90 to 100% ethyl acetate/petrol
  12. customThe title compound was further purified by trituration with dichloromethane

Sources & evidence

ORD record
ord-3509d24df6a84475a82ae0da7c3057ae
Source dataset
uspto-grants-2010_08
Patent number
US07767672B2

Reaction notes

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