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

Participants

Role	Name	HCID	Charge
Reactant	Quinolin-5-ylboronic acid	HCID 5153389	—
Reactant	6-Chloro-N-(3-methoxyphenyl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine	HCID 46261794	—
Product	N-(3-methoxyphenyl)-1-methyl-6-(quinolin-5-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine	HCID 44181587	—

Reaction Steps

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

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08987280B2
Source dataset	uspto-grants-2015_03
ORD ID	ord-a63d453330bf412db0a948890773bb3b
Source note	uspto-grants-2015_03