5-(2-trimethylsilanyl-ethoxymethyl)-2-trimethylstannanyl-5H-pyrrolo[2,3-b]pyrazine → [(S)-1-(2-methyl-propane-1-sulfonyl)-piperidin-3-yl]-[5-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyrimidin-4-yl]-amine
Reaction equation
Br[C:2]1[C:3]([NH:10][C@H:11]2[CH2:16][CH2:15][CH2:14][N:13]([S:17]([CH2:20][CH:21]([CH3:23])[CH3:22])(=[O:19])=[O:18])[CH2:12]2)=[N:4][C:5](SC)=[N:6][CH:7]=1.C[Si](C)(C)CCOC[N:30]1[C:34]2=[N:35][CH:36]=[C:37]([Sn](C)(C)C)[N:38]=[C:33]2[CH:32]=[CH:31]1>>[CH3:22][CH:21]([CH3:23])[CH2:20][S:17]([N:13]1[CH2:14][CH2:15][CH2:16][C@H:11]([NH:10][C:3]2[C:2]([C:37]3[N:38]=[C:33]4[CH:32]=[CH:31][NH:30][C:34]4=[N:35][CH:36]=3)=[CH:7][N:6]=[CH:5][N:4]=2)[CH2:12]1)(=[O:19])=[O:18]Participants
3
Reactant 2
Product 1
Procedure
Starting with (5-bromo-2-methylsulfanyl-pyrimidin-4-yl)-[(S)-1-(2-methyl-propane-1-sulfonyl)-piperidin-3-yl]-amine from above and 5-(2-trimethylsilanyl-ethoxymethyl)-2-trimethylstannanyl-5H-pyrrolo[2,3-b]pyrazine described in step 3 of Example 76, and using similar synthetic procedures of steps 4-5 described herein from Example 76, gave [(S)-1-(2-methyl-propane-1-sulfonyl)-piperidin-3-yl]-[5-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyrimidin-4-yl]-amine. MS (ES+): 416.
Sources & evidence
- ORD record
- ord-a407985b611c4972a3e5a13d1407a83b
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08618103B2
Reaction notes
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