4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → 4-(5-(2-(Dimethylamino)ethoxy)pyrimidin-2-yl)phenol

Participants

Role	Name	HCID	Charge
Reactant	4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol	HCID 2734624	—
Reactant	4-(Hydroxymethyl)benzeneboronic acid	HCID 2734706	—
Reactant	ethyl 2-(8-(benzo[d]thiazol-2-yl((2-(trimethylsilyl)ethoxy)methyl)carbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-5-(4-(hydroxymethyl)phenyl)thiazole-4-carboxylate	HCID 59447480	—
Reactant	2-(2-chloropyrimidin-5-yloxy)-N,N-dimethylethanamine	HCID 59447495	—
Product	4-(5-(2-(Dimethylamino)ethoxy)pyrimidin-2-yl)phenol	HCID 136027727	—

Reaction Steps

Compound 112C was prepared in a similar manner to the synthesis of compound 34D by substituting compound 34C and 4-(hydroxymethyl)phenylboronic acid with compound 112B and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol, respectively: 1H NMR (DMSO-d6): δ 9.80 (s, 1H), 8.56 (s, 2H), 8.12-8.15 (m, 1H), 6.83-6.86 (m, 2H), 4.23 (t, J=5.8 Hz, 2H), 2.65 (t, J=5.65 Hz, 2H), 2.22 (s, 6H); ESI (+)/MS: 259 (M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08232273B2
Source dataset	uspto-grants-2012_07
ORD ID	ord-29694404005146969fcf53b08004f1c8
Source note	uspto-grants-2012_07