3-Methyl-1-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]urea → 1-(4-(5-(6-chloro-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-chloro-2,3-dihydro-1H-inden-1-yl)-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one	HCID 86670116	—
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-chloro-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 68195405	—

Reaction Steps

The title compound was prepared in a manner similar to EXAMPLE 84 using 2-chloro-5-(6-chloro-2,3-dihydro-1H-inden-1-yl)-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one (PREPARATION x41, 90 mg, 0.230 mmol), 1-methyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea (127 mg, 0.460 mmol) and PdCl2(dppf) (8.42 mg, 0.012 mmol) in dioxane (2 mL) and aqueous saturated NaHCO3 (0.4 mL). 1H NMR (400 MHz, DMSO-d6) δ 2.36-2.45 (m, 2 H), 2.62-2.66 (d, 3 H), 3.08-3.22 (m, 3 H), 3.55-3.67 (m, 3 H), 3.95-4.10 (m, 1 H), 4.13-4.30 (m, 1 H), 4.38-4.66 (m, 2 H), 6.03-6.16 (m, 1 H), 7.14-7.43 (m, 4 H), 7.43-7.52 (d, 2 H), 8.03-8.16 (d, 2 H), 8.72-8.82 (m, 1 H). ESI-MS m/z [M+H]+ calc'd for C26H25ClN6O3, 505.17; found 505.4.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09045496B2
Source dataset	uspto-grants-2015_06
ORD ID	ord-fbd6ff37d726408993af22298c2a08be
Source note	uspto-grants-2015_06