3-Pyridinylboronic acid → HCID 44181709, compound

HRID 876924Notes

Reaction equation

HRID 876924 reaction equation
Cl[C:2]1[N:7]=[C:6]2[N:8]([CH3:11])[N:9]=[CH:10][C:5]2=[C:4]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=2)[N:3]=1.[N:21]1[CH:26]=[CH:25][CH:24]=[C:23](B(O)O)[CH:22]=1>>[CH3:20][O:19][C:15]1[CH:14]=[C:13]([NH:12][C:4]2[N:3]=[C:2]([C:23]3[CH:22]=[N:21][CH:26]=[CH:25][CH:24]=3)[N:7]=[C:6]3[N:8]([CH3:11])[N:9]=[CH:10][C:5]=23)[CH:18]=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 27343783-Pyridinylboronic acidHCID 462617946-Chloro-N-(3-methoxyphenyl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Product 1

HCID 44181709HCID 44181709, compound

Procedure

6-Chloro-N-(3-methoxyphenyl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine 6, from Example 4, was reacted with pyridine-3-boronic acid using General Procedure A. Purification on silica yielded 124. NMR: (CDCl3): 3.88 (s, 3H, CH3), 4.13 (s, 3H, CH3), 6.88-6.90 (m, H, ArH), 7.16 (m, H, ArH), 7.30 (s, H, ArH), 7.38-7.46 (m, 2H, 2×ArH), 7.50 (sbr, H, NH), 8.72 (m, H, ArH), 8.79-8.82 (m, H, ArH) 9.76 (m, H, ArH). MS: (ESI+) MH+=333.24

Workup

  1. customPurification on silica

Sources & evidence

ORD record
ord-a60ff648c84947fd8c4e28825846108e
Source dataset
uspto-grants-2015_03
Patent number
US08987280B2

Reaction notes

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