4-Bromo-1-isoquinolinamine → 4-(8-((4-tert-butylpiperidin-1-yl)methyl)-9-methyl-6-morpholino-9H-purin-2-yl)isoquinolin-1-amine
Reaction equation
[C:1]([CH:5]1[CH2:10][CH2:9][N:8]([CH2:11][C:12]2[N:13]([CH3:40])[C:14]3[C:19]([N:20]=2)=[C:18]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[N:17]=[C:16]([Sn](CCCC)(CCCC)CCCC)[N:15]=3)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].Br[C:42]1[C:51]2[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=2)[C:45]([NH2:52])=[N:44][CH:43]=1>>[C:1]([CH:5]1[CH2:6][CH2:7][N:8]([CH2:11][C:12]2[N:13]([CH3:40])[C:14]3[C:19]([N:20]=2)=[C:18]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[N:17]=[C:16]([C:42]2[C:51]4[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=4)[C:45]([NH2:52])=[N:44][CH:43]=2)[N:15]=3)[CH2:9][CH2:10]1)([CH3:4])([CH3:2])[CH3:3]Participants
3
Procedure
4-(8-((4-tert-butylpiperidin-1-yl)methyl)-9-methyl-2-(tributylstannyl)-9H-purin-6-yl)morpholine (0.1 g) was reacted with 4-bromoisoquinolin-1-amine via General Procedure D to afford 114 (10 mg) following reverse phase purification. MS (Q1) 515.3 (M)+. 1H NMR (500 MHz, CDCl3) δ 9.02 (d, 1H), 7.94-7.45 (m, 6H), 4.35 (s, 4H), 4.02-3.61 (m, 9H), 2.97 (s, 2H), 2.13 (s, 2H), 1.92-1.52 (m, 5H), 1.52-0.68 (m, 26H)
Sources & evidence
- ORD record
- ord-f4a4e1f028c645778380eadb69cdc89e
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08173650B2
Reaction notes
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