Triethylamine → 2-Iodo-N-(4-(4-(oxetan-3-yl)piperazin-1-yl)phenyl)-9-((2-(trimethylsilyl)ethoxy)methyl)-9H-purin-6-amine

HRID 1024078Notes

Reaction equation

Cl[C:2]1[N:10]=[C:9]([I:11])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17].[O:20]1[CH2:23][CH:22]([N:24]2[CH2:29][CH2:28][N:27]([C:30]3[CH:36]=[CH:35][C:33]([NH2:34])=[CH:32][CH:31]=3)[CH2:26][CH2:25]2)[CH2:21]1.C(N(CC)CC)C>C(O)(C)C>[I:11][C:9]1[N:8]=[C:7]2[C:3]([N:4]=[CH:5][N:6]2[CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])=[C:2]([NH:34][C:33]2[CH:32]=[CH:31][C:30]([N:27]3[CH2:28][CH2:29][N:24]([CH:22]4[CH2:23][O:20][CH2:21]4)[CH2:25][CH2:26]3)=[CH:36][CH:35]=2)[N:10]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 117b (2.05 g, 5.0 mmol), 117e (1.17 g, 5.0 mmol), and triethylamine (1.01 g, 10 mmol) in i-propanol (30 mL) was stirred at 80° C. for 4 h. It was then filtered and the filtrate was evaporated in vacuo. The residue was purified by silica-gel column chromatography eluting with 30:1 dichloromethane/methanol to afford 117f (1.82 g, 60%) as a yellow solid. MS-ESI: [M+H]+ 608.1

Workup

filtrationIt was then filtered
customthe filtrate was evaporated in vacuo
customThe residue was purified by silica-gel column chromatography
washeluting with 30:1 dichloromethane/methanol

Sources & evidence

ORD record: ord-d2e9ad2ce19b4b2e954b24b2dee9fa8d
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722676B2

Reaction notes

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