5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinonitrile → 5-(4-Morpholino-6-((piperazin-1-yl)methyl)thieno[3,2-d]pyrimidin-2-yl)pyridine-3-carbonitrile

Participants

Role	Name	HCID	Charge
Reactant	5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinonitrile	HCID 16414216	—
Reactant	4-(2-Chloro-6-((4-(methylsulfonyl)piperazin-1-yl)methyl)thieno[3,2-d]pyrimidin-4-yl)morpholine	HCID 23650837	—
Product	5-(4-Morpholino-6-((piperazin-1-yl)methyl)thieno[3,2-d]pyrimidin-2-yl)pyridine-3-carbonitrile	HCID 66934265	—

Reaction Steps

2-Chloro-6-(4-methanesulfonyl-piperazin-1-ylmethyl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidine, prepared via General Procedure B-3, was reacted with 3-cyanopyridine-5-boronic acid pinacol ester via General Procedure A. Purification on silica yielded 170. (400 MHz CDCl3): 2.68-2.71 (4H, m, CH2), 2.81 (3H, s, CH3), 3.30-3.32 (4H, m, CH2), 3.90-3.92 (6H, m, CH2), 4.06-4.08 (4H, m, CH2), 7.35 (1H, s, ar), 8.92 (1H, d (J=2.09), ar), 8.96-8.97 (1H, m, ar), 9.81 (1H, d (J=2.03), ar). MH+ 500.20

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08383620B2
Source dataset	uspto-grants-2013_02
ORD ID	ord-e26e1e15f7ac4f849a98a340e58b132c
Source note	uspto-grants-2013_02