5-Chloropyridine-3-boronic acid → 4-(2-(2-(5-chloropyridin-3-yl)-9-isopropyl-9H-purin-6-ylamino)ethyl)phenol

HRID 1422482Notes

Reaction equation

HRID 1422482 reaction equation
I[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:11]([CH3:13])[CH3:12])=[C:4]([NH:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)[N:3]=1.[Cl:24][C:25]1[CH:26]=[C:27](B(O)O)[CH:28]=[N:29][CH:30]=1>>[Cl:24][C:25]1[CH:26]=[C:27]([C:2]2[N:10]=[C:9]3[C:5]([N:6]=[CH:7][N:8]3[CH:11]([CH3:13])[CH3:12])=[C:4]([NH:14][CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=3)[N:3]=2)[CH:28]=[N:29][CH:30]=1

Participants

3

Reactant 2

HCID 201118775-Chloropyridine-3-boronic acidHCID 866434604-(2-(2-iodo-9-isopropyl-9H-purin-6-ylamino)ethyl)phenol

Product 1

HCID 594089024-(2-(2-(5-chloropyridin-3-yl)-9-isopropyl-9H-purin-6-ylamino)ethyl)phenol

Procedure

Following the procedure of Example 15d, 4-(2-(2-iodo-9-isopropyl-9H-purin-6-ylamino)ethyl)phenol (b) was reacted with 5-chloropyridin-3-ylboronic acid. The crude product was purified by reverse-phase HPLC(C18 column, eluting with ACN—H2O 0.05% TFA) to afford the title compound as an off-white solid.

Workup

  1. customThe crude product was purified by reverse-phase HPLC(C18 column
  2. washeluting with ACN—H2O 0.05% TFA)

Sources & evidence

ORD record
ord-045430049ca74ad394c835b626cf5ffc
Source dataset
uspto-grants-2015_01
Patent number
US08927281B2

Reaction notes

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