Potassium Phosphate, Tribasic → 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

Participants

Role	Name	HCID	Charge
Reactant	Potassium Phosphate, Tribasic	HCID 62657	—
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Reactant	4-(5-bromo-2-chloropyrimidin-4-yl)-N-(6-chloro-2,3-dihydro-1H-inden-1-yl)morpholine-3-carboxamide	HCID 86670115	—
Catalyst	palladium(II) acetate	HCID 167845	—
Solvent	tert-Butanol	HCID 6386	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	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	—

Reaction Steps

The title compound was prepared in a manner similar to PREPARATION x35 using 4-(5-bromo-2-chloropyrimidin-4-yl)-N-(6-chloro-2,3-dihydro-1H-inden-1-yl)morpholine-3-carboxamide (PREPARATION x40, 567 mg, 1.201 mmol), Xantphos (52.1 mg, 0.090 mmol), palladium(II)acetate (13.48 mg, 0.060 mmol) and potassium phosphate (255 mg, 1.201 mmol) in dioxane (5 mL) and tert-butanol (1 mL). 1H NMR (400 MHz, DMSO-d6) δ 2.21-2.48 (m, 3H), 2.87-3.05 (m, 2H), 3.05-3.21 (m, 1H), 3.47-3.65 (m, 2H), 3.88-4.01 (m, 1H), 4.08-4.32 (m, 2H), 4.39-4.56 (m, 1H), 7.16-7.42 (m, 4H). ESI-MS m/z [M+H]+ calc'd for C18H16Cl2N4O2, 391.07. found 391.3.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08791107B2
Source dataset	uspto-grants-2014_07
ORD ID	ord-2cd8f7a5f6d14cafa109b9703e7e2711
Source note	uspto-grants-2014_07