2-bromo-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine → 3-((S)-3-{2-methylsulfanyl-5-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-pyrimidin-4-ylamino}-piperidin-1-yl)-3-oxo-propionitrile

HRID 1916138Notes

Reaction equation

HRID 1916138 reaction equation
Br[C:2]1[C:3]([NH:10][C@H:11]2[CH2:16][CH2:15][CH2:14][N:13]([C:17](=[O:21])[CH2:18][C:19]#[N:20])[CH2:12]2)=[N:4][C:5]([S:8][CH3:9])=[N:6][CH:7]=1.[CH3:22][Si:23]([CH3:42])([CH3:41])[CH2:24][CH2:25][O:26][CH2:27][N:28]1[C:32]2=[N:33][CH:34]=[C:35]([Sn](C)(C)C)[N:36]=[C:31]2[CH:30]=[CH:29]1.BrC1N=C2C=CN(COCC[Si](C)(C)C)C2=NC=1>>[CH3:9][S:8][C:5]1[N:4]=[C:3]([NH:10][C@H:11]2[CH2:16][CH2:15][CH2:14][N:13]([C:17](=[O:21])[CH2:18][C:19]#[N:20])[CH2:12]2)[C:2]([C:35]2[N:36]=[C:31]3[CH:30]=[CH:29][N:28]([CH2:27][O:26][CH2:25][CH2:24][Si:23]([CH3:42])([CH3:41])[CH3:22])[C:32]3=[N:33][CH:34]=2)=[CH:7][N:6]=1

Participants

4

Reactant 3

HCID 575165972-bromo-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazineHCID 581774595-(2-trimethylsilanyl-ethoxymethyl)-2-trimethylstannanyl-5H-pyrrolo[2,3-b]pyrazineHCID 69813505HCID 69813505, compound

Product 1

HCID 698122873-((S)-3-{2-methylsulfanyl-5-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-pyrimidin-4-ylamino}-piperidin-1-yl)-3-oxo-propionitrile

Procedure

The 3-[(S)-3-(5-bromo-2-methylsulfanyl-pyrimidin-4-ylamino)-piperidin-1-yl]-3-oxo-propionitrile from above (226 mg, 609 μmol) was cross-coupled with 5-(2-trimethylsilanyl-ethoxymethyl)-2-trimethylstannanyl-5H-pyrrolo[2,3-b]pyrazine prepared from 2-bromo-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine (200 mg, 0.61 mmol) and tetrakistriphenylphosphine palladium (0) (35 mg, 0.03 mmol) in a manner similar to step 3, Example 76 to give 3-((S)-3-{2-methylsulfanyl-5-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-pyrimidin-4-ylamino}-piperidin-1-yl)-3-oxo-propionitrile (−40 mg). MS (ES+): 539.

Sources & evidence

ORD record
ord-fc3fc75bae4e49d19a49de85b11e9bf0
Source dataset
uspto-grants-2013_12
Patent number
US08618103B2

Reaction notes

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