Hydrochloric Acid → 5-(3-Bromo-phenyl)-7-methylsulfanyl-pyrazolo[1,5-c]pyrimidine

HRID 19611Notes

Reaction equation

HRID 19611 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[NH:13][C:12](=[S:14])[N:11]3[N:15]=[CH:16][CH:17]=[C:10]3[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:18]I.Cl>[OH-].[Na+].CO>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]=[C:12]([S:14][CH3:18])[N:11]3[N:15]=[CH:16][CH:17]=[C:10]3[CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 178527900HCID 178527900, compound2×

Product 1

HCID 673192425-(3-Bromo-phenyl)-7-methylsulfanyl-pyrazolo[1,5-c]pyrimidineYield 36%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 5-(3-bromo-phenyl)-6H-pyrazolo[1,5-c]pyrimidine-7-thione (compound E3)(3.73 g) in 2M aqueous NaOH (6 ml) and methanol (100 ml) methyl iodide (0.785 ml) is added at ambient temperature. After 30 min at this temperature further methyl iodide (0.785 ml) is added After 60 min the mixture is neutralized with 2M hydrochloric acid and evaporated The residue is partitioned between dichloromethane and water and the organic phase is washed twice with water. The organic phase is dried over sodium sulfate and the crude product is purified by silica gel flash chromatography. A yellow solid (1.4 g, 36%) is obtained

Workup

  1. customevaporated The residue
  2. customis partitioned between dichloromethane and water
  3. washthe organic phase is washed twice with water
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. customthe crude product is purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-5b3b51c436064958806e0e7c7870c593
Source dataset
uspto-grants-2010_06
Patent number
US07745446B2

Reaction notes

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