Water → 1-methyl-3-(2-methylsulfanylpyrimidin-4-yl)-1H-indazole

HRID 1946978Notes

Reaction equation

HRID 1946978 reaction equation
[H-].[Na+].[CH3:3][S:4][C:5]1[N:10]=[C:9]([C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[NH:13][N:12]=2)[CH:8]=[CH:7][N:6]=1.[CH3:20]I.O>CN1C(=O)CCC1>[CH3:20][N:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11]([C:9]2[CH:8]=[CH:7][N:6]=[C:5]([S:4][CH3:3])[N:10]=2)=[N:12]1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 597433513-(2-methylsulfanyl-pyrimidin-4-yl)-1H-indazole

Product 1

HCID 597434781-methyl-3-(2-methylsulfanylpyrimidin-4-yl)-1H-indazoleYield 75.3%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Sodium hydride (60% suspension in mineral oil, 99 mg, 2.47 mmol) was added to a stirring solution of 3-(2-methylsulfanyl-pyrimidin-4-yl)-1H-indazole (520 mg, 2.15 mmol) in NMP at 0° C. The mixture was stirred for 15 min and then methyliodide (0.14 mL, 2.25 mmol) was added and the resulting mixture was stirred for 2 h. The reaction mixture was then poured into water and extracted twice with EtOAc. The combined organic extracts were dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography (hexane/EtOAc, 9/1) to give 415 mg of 1-methyl-3-(2-methylsulfanylpyrimidin-4-yl)-1H-indazole.

Workup

  1. stirringthe resulting mixture was stirred for 2 h
  2. extractionextracted twice with EtOAc
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residue was purified by flash chromatography (hexane/EtOAc, 9/1)

Sources & evidence

ORD record
ord-a96760cb0acf4c018fe8271b730b93ae
Source dataset
uspto-grants-2013_03
Patent number
US08399462B2

Reaction notes

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