3-Methyl-1-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]urea → 1-(4-(5-(2-Chloro-4-(methylsulfonyl)benzyl)-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridin-2-yl)phenyl)-3-methylurea

Participants

Role	Name	HCID	Charge
Reactant	3-Methyl-1-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]urea	HCID 17750273	—
Reactant	2-Chloro-5-(2-chloro-4-(methylsulfonyl)benzyl)-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine	HCID 86670090	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	1,4-Dioxane	HCID 31275	—
Solvent	Sodium Bicarbonate	HCID 516892	—
Product	1-(4-(5-(2-Chloro-4-(methylsulfonyl)benzyl)-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridin-2-yl)phenyl)-3-methylurea	HCID 60197762	—

Reaction Steps

The title compound was prepared in a manner similar to EXAMPLE 5 using 2-chloro-5-(2-chloro-4-(methylsulfonyl)benzyl)-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine (PREPARATION x6, 175 mg, 0.408 mmol), (1-methyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea (225 mg, 0.815 mmol) and PdCl2(dppf) (14.91 mg, 0.020 mmol) in dioxane (5 mL) and aqueous saturated NaHCO3 (1 mL). 1H NMR (400 MHz, DMSO-d6) δ 2.61-2.71 (m, 3 H), 3.28-3.31 (m, 2 H), 3.53-3.66 (m, 1 H), 3.87-4.02 (m, 2 H), 4.03-4.15 (m, 1 H), 4.59-4.79 (m, 2 H), 4.79-4.91 (m, 1 H), 6.14-6.25 (m, 1 H), 7.32-7.38 (m, 1 H), 7.53-7.62 (m, 2 H), 7.63-7.71 (m, 1 H), 7.81-7.90 (m, 1 H), 7.99-8.12 (m, 3 H), 8.91-9.05 (m, 1 H). ESI-MS m/z [M+H]+ calc'd for C25H27ClN6O4S, 543.15; found 543.5.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09045496B2
Source dataset	uspto-grants-2015_06
ORD ID	ord-ed85ad6ae6af4c259e194466947585b7
Source note	uspto-grants-2015_06