4-Phenoxyphenylboronic acid → (E)-1-((3S,4S)-4-(((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)amino)methyl)-3-hydroxypiperidin-1-yl)-4-(dimethylamino)but-2-en-1-one

Participants

Role	Name	HCID	Charge
Reactant	4-Phenoxyphenylboronic acid	HCID 2734377	—
Reactant	trans-1-Boc-4-aminomethyl-3-hydroxypiperidine	HCID 11075229	—
Reactant	5,6-Dichloro-pyrimidin-4-ylamine	HCID 24219262	—
Reactant	(2E)-4-(Dimethylamino)-2-butenoic acid hydrochloride	HCID 45358758	—
Product	(E)-1-((3S,4S)-4-(((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)amino)methyl)-3-hydroxypiperidin-1-yl)-4-(dimethylamino)but-2-en-1-one	HCID 71092950	—

Reaction Steps

(E)-1-((3S,4S)-4-(((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)amino)methyl)-3-hydroxypiperidin-1-yl)-4-(dimethylamino)but-2-en-1-one was prepared from 5,6-dichloropyrimidin-4-amine, (3S,4S)-tert-butyl 4-(aminomethyl)-3-hydroxypiperidine-1-carboxylate, (4-phenoxyphenyl)boronic acid and (E)-4-(dimethylamino)but-2-enoic acid hydrochloride according to general scheme 3 using methods S1, S2, S3, and S4D. HPLC purity: 99%. MS: m/z=503 [M+H]+. 1H NMR (CD3OD) δ 8.26 (s, 1H), 7.10-7.45 (m, 9H), 6.91 (d, 1H), 6.67 (m, 1H), 4.54 (m, 1H), 4.02 (m, 1H), 3.97 (m, 2H), 3.74 (m, 1H), 3.51 (m, 1H), 3.00 (m, 1H), 2.62 (m, 1H), 1.76 (m, 2H), 1.23 (m, 1H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09073947B2
Source dataset	uspto-grants-2015_07
ORD ID	ord-4b3a7597e441438ab250e71ac2d2a0a4
Source note	uspto-grants-2015_07