Ethanol → ((S)-1-methanesulfonyl-piperidin-3-yl)-{5-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-pyrimidin-4-yl}-amine

HRID 1916118Notes

Reaction equation

HRID 1916118 reaction equation
[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][CH2:8][C@H:7]([NH:11][C:12]2[C:17]([C:18]3[N:19]=[C:20]4[CH:26]=[CH:25][N:24]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[C:21]4=[N:22][CH:23]=3)=[CH:16][N:15]=[C:14](SC)[N:13]=2)[CH2:6]1)(=[O:4])=[O:3].C(O)C.O>O1CCOCC1.[Ni]>[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][CH2:8][C@H:7]([NH:11][C:12]2[C:17]([C:18]3[N:19]=[C:20]4[CH:26]=[CH:25][N:24]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[C:21]4=[N:22][CH:23]=3)=[CH:16][N:15]=[CH:14][N:13]=2)[CH2:6]1)(=[O:4])=[O:3]

Participants

6

Reactant 3

HCID 702EthanolHCID 962WaterHCID 69812827((S)-1-methanesulfonyl-piperidin-3-yl)-{2-methylsulfanyl-5-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-pyrimidin-4-yl}-amine

Product 1

HCID 69811925((S)-1-methanesulfonyl-piperidin-3-yl)-{5-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-pyrimidin-4-yl}-amineYield 21.8%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 312751,4-DioxaneSolvent

Procedure

((S)-1-methanesulfonyl-piperidin-3-yl)-{2-methylsulfanyl-5-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-pyrimidin-4-yl}-amine (400 mg, 0.728 mmol) was dissolved in dioxane (10 ml), ethanol (2 ml) and water (2 ml) and treated with 2 g of Raney Nickel (2000). This was refluxed for 16 hours. The reaction was filtered, evaporated and purified by silica gel chromatography (5% methanol/methylene chloride to give ((S)-1-methanesulfonyl-piperidin-3-yl)-{5-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-pyrimidin-4-yl}-amine (˜80 mg). MS (ES+): 504.

Workup

  1. temperatureThis was refluxed for 16 hours
  2. filtrationThe reaction was filtered
  3. customevaporated
  4. custompurified by silica gel chromatography (5% methanol/methylene chloride

Sources & evidence

ORD record
ord-7c12f3862c7148e09f26c45bca9119fe
Source dataset
uspto-grants-2013_12
Patent number
US08618103B2

Reaction notes

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