5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine → 5-(4-morpholino-6-(1-(4-N-methylsulfonylpiperazin-1-yl)ethyl)thieno[3,2-d]pyrimidin-2-yl)pyridin-2-amine

Participants

Role	Name	HCID	Charge
Reactant	5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine	HCID 2756555	—
Reactant	2-Chloro-6-[1-(4-methanesulfonyl-piperazin-1-yl)-ethyl]-4-morpholin-4-yl-thieno[3,2-d]pyrimidine	HCID 86618431	—
Product	5-(4-morpholino-6-(1-(4-N-methylsulfonylpiperazin-1-yl)ethyl)thieno[3,2-d]pyrimidin-2-yl)pyridin-2-amine	HCID 58233863	—

Reaction Steps

2-Chloro-6-[1-(4-methanesulfonyl-piperazin-1-yl)-ethyl]-4-morpholin-4-yl-thieno[3,2-d]pyrimidine was reacted with 2-amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine in General Procedure A. Purification on silica yielded 299. NMR: (CDCl3): 1.43 (3H, d, J 7.2, Me), 2.56-2.68 (4H, m, CH2), 2.73 (3H, s, Me), 3.18-3.29 (4H, m, CH2), 3.80-3.83 (4H, m, CH2), 3.94-3.99 (5H, m), 4.58 (2H, br s, NH2), 6.48 (1H, d, J 8.1, Ar), 7.19 (1H, s, Ar), 8.38 (1H, dd, J 8.1 and 2.0, Ar) and 9.07 (1H, d, J 2.0, Ar). MS: (ESI+): MH+=504.26

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07888352B2
Source dataset	uspto-grants-2011_02
ORD ID	ord-8d6fb26005a440a6a7b08acb8c6f202f
Source note	uspto-grants-2011_02