4-Phenoxyphenylboronic acid → (E)-1-(2-((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)amino)-6-azaspiro[3.4]octan-6-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	(2E)-4-(Dimethylamino)-2-butenoic acid hydrochloride	HCID 45358758	—
Reactant	tert-Butyl 2-amino-6-azaspiro[3.4]octane-6-carboxylate	HCID 56962195	—
Product	(E)-1-(2-((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)amino)-6-azaspiro[3.4]octan-6-yl)-4-(dimethylamino)but-2-en-1-one	HCID 71092925	5.4%

Reaction Steps

(E)-1-(2-((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)amino)-6-azaspiro[3.4]octan-6-yl)-4-(dimethylamino)but-2-en-1-one was prepared 5,6-dichloropyrimidin-4-amine, 4-phenoxyphenylboronic acid, tert-butyl 2-amino-6-azaspiro[3.4]octane-6-carboxylate and (E)-4-(dimethylamino)but-2-enoic acid hydrochloride with method S1, S2, S3, S4A. Yield 5.4%. 1H NMR (CD3OD) δ 8.31 (s, 1H), 7.10-7.47 (m, 9H), 6.75 (m, 2H), 3.97 (m, 2H), 3.65 (m, 1H), 3.50 (m, 1H), 2.92 (m, 6H), 2.38 (m, 2H), 2.12 (m, 2H), 2.0 (t, 1H), 1.80 (m, 2H), 1.62 (m, 2H). HPLC PURITY: 98%, MS: m/z=499[M+H]+

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09073947B2
Source dataset	uspto-grants-2015_07
ORD ID	ord-9aee8334a11f4a69bf2254fc4d304aa1
Source note	uspto-grants-2015_07