3-Methyl-1-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]urea → 1-(4-(5-(6-methoxy-2,3-dihydro-1H-inden-1-yl)-6-oxo-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-(6-methoxy-2,3-dihydro-1H-inden-1-yl)-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one	HCID 86670118	—
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-(6-methoxy-2,3-dihydro-1H-inden-1-yl)-6-oxo-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridin-2-yl)phenyl)-3-methylurea	HCID 68194608	—

Reaction Steps

The title compound was prepared in a manner similar to EXAMPLE 84 using 2-chloro-5-(6-methoxy-2,3-dihydro-1H-inden-1-yl)-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one (PREPARATION x43, 70 mg, 0.181 mmol), 1-methyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea (100 mg, 0.362 mmol) and PdCl2(dppf) (6.62 mg, 9.05 μmol) in dioxane (3 mL) and aqueous saturated NaHCO3 (0.6 mL). 1H NMR (400 MHz, DMSO-d6) δ 2.23-2.45 (m, 3 H), 2.60-2.66 (m, 3 H), 2.87-3.17 (m, 4 H), 3.55-3.72 (m, 4 H), 3.95-4.10 (m, 1 H), 4.16-4.34 (m, 1 H), 4.38-4.64 (m, 2 H), 6.04-6.15 (m, 1 H), 6.49-6.91 (m, 3 H), 7.23-7.34 (m, 1 H), 7.41-7.50 (m, 2 H), 8.04-8.14 (m, 2 H), 8.72-8.81 (m, 1 H). ESI-MS m/z [M+H]+ calc'd for C27H28N6O4, 501.22; found 501.5.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09045496B2
Source dataset	uspto-grants-2015_06
ORD ID	ord-eff24ea23d634bdc9ae9b83443349426
Source note	uspto-grants-2015_06