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

Participants

Role	Name	HCID	Charge
Reactant	4-Phenoxyphenylboronic acid	HCID 2734377	—
Reactant	5,6-Dichloro-pyrimidin-4-ylamine	HCID 24219262	—
Reactant	tert-Butyl 4-aminomethyl-4-fluoropiperidine-1-carboxylate	HCID 40152119	—
Reactant	(2E)-4-(Dimethylamino)-2-butenoic acid hydrochloride	HCID 45358758	—
Product	(E)-1-(4-(((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)amino)methyl)-4-fluoropiperidin-1-yl)-4-(dimethylamino)but-2-en-1-one	HCID 71093096	15.9%

Reaction Steps

(E)-1-(4-(((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)amino)methyl)-4-fluoropiperidin-1-yl)-4-(dimethylamino)but-2-en-1-one was prepared 5,6-dichloropyrimidin-4-amine, 4-phenoxyphenylboronic acid, tert-butyl 4-(aminomethyl)-4-fluoropiperidine-1-carboxylate and (E)-4-(dimethylamino)but-2-enoic acid hydrochloride with method S1, S2, S3, S4A. Yield 15.9%. 1H NMR (CD3OD) δ 8.26 (s, 1H), 7.14-7.40 (m, 9H), 6.93 (d, 1H), 6.74 (m, 1H), 4.47 (d, 1H), 3.98 (m, 3H), 3.75 (d, 2H), 3.41 (t, 1H), 3.03 (t, 1H), 2.97 (m, 6H), 1.81 (m, 2H), 1.62 (m, 2H). HPLC PURITY: 99%, MS: m/z=505[M+H]+

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09073947B2
Source dataset	uspto-grants-2015_07
ORD ID	ord-573ac6401ac54e2398da7d13835bfba8
Source note	uspto-grants-2015_07