(Pyrimidin-5-yl)boronic acid → N,1-dimethyl-N-((4-morpholino-2-(pyrimidin-5-yl)thieno[2,3-d]pyrimidin-6-yl)methyl)piperidin-4-amine

Participants

Role	Name	HCID	Charge
Reactant	(Pyrimidin-5-yl)boronic acid	HCID 2795193	—
Reactant	N-((2-chloro-4-morpholinothieno[2,3-d]pyrimidin-6-yl)methyl)-N,1-dimethylpiperidin-4-amine	HCID 86623517	—
Product	N,1-dimethyl-N-((4-morpholino-2-(pyrimidin-5-yl)thieno[2,3-d]pyrimidin-6-yl)methyl)piperidin-4-amine	HCID 58234003	—

Reaction Steps

(2-Chloro-4-morpholin-4-yl-thieno[2,3-d]pyrimidin-6-ylmethyl)-methyl-(1-methyl-piperidin-4-yl)-amine was reacted with pyrimidine-5-boronic acid in General Procedure A. Purification on silica yielded 168. NMR (CDCl3): 1.59-1.81 (4H, m), 1.96-2.03 (2H, m), 2.25 (3H, s, Me), 2.28 (3H, s, Me), 2.44-2.52 (1H, m), 2.90-2.95 (2H, m), 3.80-3.88 (6H, m, CH2), 3.90-3.94 (4H, m, CH2), 7.10 (1H, s, Ar), 9.16 (1H, s, Ar) and 9.60 (2H, s, Ar). MS: (ESI+): MH+ 440.22

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08383620B2
Source dataset	uspto-grants-2013_02
ORD ID	ord-565852e865aa44fab6e5b3491b35820c
Source note	uspto-grants-2013_02