Stannane, tributyl[5-(1,3-dioxolan-2-yl)-2-furanyl]- → (1-Benzyl-1H-indazol-5-yl)-(6-(5-[1,3-dioxolan-2-yl]-furan-2-yl)-pyrido[3,4-d]pyrimidin-4-yl)-amine

Participants

Role	Name	HCID	Charge
Reactant	Stannane, tributyl[5-(1,3-dioxolan-2-yl)-2-furanyl]-	HCID 10960952	—
Reactant	(1-Benzyl-1H-indazol-5-yl)-(6-chloropyrido[3,4-d]pyrimidin-4-yl)-amine	HCID 21952012	—
Catalyst	(Butane-1,4-diyl)bis(diphenylphosphane)--dichloropalladium (1/1)	HCID 10974057	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	(1-Benzyl-1H-indazol-5-yl)-(6-(5-[1,3-dioxolan-2-yl]-furan-2-yl)-pyrido[3,4-d]pyrimidin-4-yl)-amine	HCID 21951893	—

Reaction Steps

(1-Benzyl-1H-indazol-5-yl)-(6-chloropyrido[3,4-d]pyrimidin-4-yl)-amine (4.28 g), 2-(tributylstannyl)-5-(1,3-dioxolan-2-yl)-furan (J. Chem Soc., Chem. Commun., (1988), p 560) (10 g) and 1,4-bis(diphenylphosphino)butane palladium (II) chloride (1 g) were heated at reflux in dioxane (150 ml) for 24 hr (Procedure B). The solvent was removed in vacuo and the residue chromatographed on silica. Subsequent trituration gave the title compound as a yellow solid; [2H6]-DMSO 10.46 (1H, s), 9.17 (1H, s), 8.74 (1H, s), 8.52 (1H, s), 8.23 (1H, s), 8.18 (1H, s), 7.80-7.68 (2H, m), 7.41-7.22 (5H, m), 7.17 (1H, d), 6.80 (1H, d), 6.06 (1H, s), 5.71 (2H, s), 4.20-3.96 (4H, m).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09199973B2
Source dataset	uspto-grants-2015_12
ORD ID	ord-dcad7c518ef64496b0582519ec5ab392
Source note	uspto-grants-2015_12