Quinolin-5-ylboronic acid → N-(3-methoxyphenyl)-1-methyl-6-(quinolin-5-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 876916Notes

Reaction equation

HRID 876916 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[C:30]2[CH:29]=[CH:28][CH:27]=[C:26](B(O)O)[C:25]=2[CH:24]=[CH:23][CH:22]=1>>[CH3:20][O:19][C:15]1[CH:14]=[C:13]([NH:12][C:4]2[N:3]=[C:2]([C:26]3[CH:27]=[CH:28][CH:29]=[C:30]4[C:25]=3[CH:24]=[CH:23][CH:22]=[N:21]4)[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 5153389Quinolin-5-ylboronic acidHCID 462617946-Chloro-N-(3-methoxyphenyl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Product 1

HCID 44181587N-(3-methoxyphenyl)-1-methyl-6-(quinolin-5-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Procedure

6-Chloro-N-(3-methoxyphenyl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine 6 was reacted with 5-quinolineboronic acid using General Procedure A. Purification on silica yielded 116. NMR: (CDCl3): 3.80 (s, CH3), 4.13 (s, CH3), 6.88 (dd, H, ArH, J=2.3, 8.3), 7.07 (d, H, ArH, J=6.18), 7.22 (s, H, NH), 7.35 (t, H, ArH, J=8.1), 7.44-7.51 (m, 3H, 3×ArH), 7.85 (t, H, ArH, J=8.4), 8.25 (d, H, ArH, J=8.4), 8.29 (dd, H, ArH, J=1.1, 8.3), 8.98 (dd, H, ArH, J=1.7, 4.1), 9.26 (d, H, ArH, J=8.6). MS: (ESI+) MH+=383.21

Workup

  1. customPurification on silica

Sources & evidence

ORD record
ord-a63d453330bf412db0a948890773bb3b
Source dataset
uspto-grants-2015_03
Patent number
US08987280B2

Reaction notes

Loading…