Methanol → HCID 69815196, compound

HRID 1916121Notes

Reaction equation

HRID 1916121 reaction equation
[CH3:1][CH:2]([CH3:39])[CH2:3][S:4]([N:7]1[CH2:12][CH2:11][CH2:10][C@H:9]([NH:13][C:14]2[C:19]([C:20]3[N:21]=[C:22]4[CH:28]=[CH:27][N:26]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[C:23]4=[N:24][CH:25]=3)=[CH:18][N:17]=[C:16](SC)[N:15]=2)[CH2:8]1)(=[O:6])=[O:5].[CH3:40]O.[S:42]([O-:47])(O[O-])(=[O:44])=O.[K+].[K+]>O1CCCC1.O>[CH3:40][S:42]([C:16]1[N:15]=[C:14]([NH:13][C@H:9]2[CH2:10][CH2:11][CH2:12][N:7]([S:4]([CH2:3][CH:2]([CH3:39])[CH3:1])(=[O:5])=[O:6])[CH2:8]2)[C:19]([C:20]2[N:21]=[C:22]3[CH:28]=[CH:27][N:26]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:34])[CH3:35])[C:23]3=[N:24][CH:25]=2)=[CH:18][N:17]=1)(=[O:47])=[O:44]

Participants

6

Reactant 3

HCID 887MethanolHCID 10313463Potassium peroxymonosulphateHCID 69811119HCID 69811119, compound

Product 1

HCID 69815196HCID 69815196, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of [(S)-1-(2-methyl-propane-1-sulfonyl)-piperidin-3-yl]-{2-methylsulfanyl-5-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-pyrimidin-4-yl}-amine (650 mg, 1.1 mmol) prepared in step 2 of Example 77 above in tetrahydrofuran (5 ml) and methanol (8 ml) was treated with a solution of potassium peroxymonosulfate dissolved in water (4 ml) at 5° C. and stirred at room temperature for 16 hours. The reaction mixture was diluted with water and extracted into dichloromethane (2×). The organic layers were dried (MgSO4) and concentrated in vacuo. Purification was by chromatography (silica gel, 40 g, 5% methanol/dichloromethane) which gave {2-methanesulfonyl-5-[5-(2-trimethysilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-pyrimidin-4-yl}-[(S)-1-(2-methyl-propane-1-sulfonyl)-piperidin-3-yl]-amine as a foam ˜450 mg. MS (ES+): 623.

Workup

  1. extractionextracted into dichloromethane (2×)
  2. dry with materialThe organic layers were dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customPurification

Sources & evidence

ORD record
ord-e34dca5705134aa2b45c0580b146f20d
Source dataset
uspto-grants-2013_12
Patent number
US08618103B2

Reaction notes

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