3-Fluoro-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)aniline → (S)-1-ethyl-3-(3-fluoro-4-(7-methyl-4-(3-methylmorpholino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea

Participants

Role	Name	HCID	Charge
Reactant	3-Fluoro-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)aniline	HCID 44755207	—
Reactant	(S)-tert-butyl 2-(4-(3-ethylureido)phenyl)-4-(3-methylmorpholino)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxylate	HCID 59239149	—
Reactant	(S)-4-(2-chloro-7-methyl-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-yl)-3-methylmorpholine	HCID 86663156	—
Product	(S)-1-ethyl-3-(3-fluoro-4-(7-methyl-4-(3-methylmorpholino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea	HCID 66678785	—

Reaction Steps

Method as described for intermediate 5 using (S)-4-(2-chloro-7-methyl-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-yl)-3-methylmorpholine (intermediate 13) and as 3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline as starting materials. The reaction mixture was filtered through a celite 545 pre-packed cartridge (2.5 g), washed with methanol and solvent removed in vacuo. The residue was purified by trituration with a (9:1) mixture of petrol ether (40-60)/ethyl acetate, yielding the title compound after filtration and drying of the solid obtained (85 mg, 0.24 mmol, 67%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08785457B2
Source dataset	uspto-grants-2014_07
ORD ID	ord-d1a3a79e977c42c385410c4a36a434eb
Source note	uspto-grants-2014_07