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, 3 H), 2.87-3.05 (m, 2 H), 3.05-3.21 (m, 1 H), 3.47-3.65 (m, 2 H), 3.88-4.01 (m, 1 H), 4.08-4.32 (m, 2 H), 4.39-4.56 (m, 1 H), 7.16-7.42 (m, 4 H). 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	US09045496B2
Source dataset	uspto-grants-2015_06
ORD ID	ord-2dee65419ac646e79f3f905bf02ba11a
Source note	uspto-grants-2015_06