3-Methyl-1-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]urea → 1-(4-(5-(1-(4-Chlorophenyl)cyclopropyl)-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-(1-(4-chlorophenyl)cyclopropyl)-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one	HCID 86670112	—
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-(1-(4-Chlorophenyl)cyclopropyl)-6-oxo-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridin-2-yl)phenyl)-3-methylurea	HCID 68195063	—

Reaction Steps

The title compound was prepared in a manner similar to EXAMPLE 84 using 2-chloro-5-(1-(4-chlorophenyl)cyclopropyl)-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one (PREPARATION x36, 100 mg, 0.256 mmol), 1-methyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea (141 mg, 0.511 mmol), and PdCl2(dppf) (18.70 mg, 0.026 mmol) in dioxane (2 mL) and aqueous saturated NaHCO3 (0.4 mL). 1H NMR (400 MHz, DMSO-d6) δ 1.10-1.24 (m, 2 H), 1.46-1.60 (m, 2 H), 2.54-2.60 (d, 3 H), 2.84-3.03 (m, 1 H), 3.46-3.57 (m, 2 H), 3.91-4.00 (m, 1 H), 4.08-4.20 (m, 1 H), 4.33-4.55 (m, 2 H), 5.98-6.07 (m, 1 H), 7.01-7.17 (m, 2 H), 7.23-7.34 (m, 2 H), 7.36-7.46 (m, 2 H), 7.68-7.73 (m, 1 H), 8.02-8.13 (m, 2 H), 8.61-8.70 (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-798ca0e9cea748508c947400842c5db4
Source note	uspto-grants-2015_06