4-(Tri-n-butylstannyl)pyridine → 7-(1-Methyl-1-triethylsilanyloxyethyl)-3-[2-(pyridin-4-yl)pyrimidin-4-yl]imidazo[1,2-alpha]pyrimidine

Participants

Role	Name	HCID	Charge
Reactant	4-(Tri-n-butylstannyl)pyridine	HCID 2737318	—
Reactant	3-(2-Chloropyrimidin-4-yl)-7-(1-methyl-1-triethylsilanyloxyethyl)-imidazo[1,2-alpha]pyrimidine	HCID 87889549	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	HCID 178418397	HCID 178418397	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	7-(1-Methyl-1-triethylsilanyloxyethyl)-3-[2-(pyridin-4-yl)pyrimidin-4-yl]imidazo[1,2-alpha]pyrimidine	HCID 69560274	—

Reaction Steps

3-(2-Chloropyrimidin-4-yl)-7-(1-methyl-1-triethylsilanyloxyethyl)-imidazo[1,2-α]pyrimidine (from Example 34) (403 mg, 1.0 mmol), 4-tributylstannylpyridine (736 mg, 2.0 mmol), tetrakis(triphenylphosphine)palladium(0) (115 mg, 10 mol %) and copper(I) iodide (115 mg) in 1,4-dioxane (20 ml) were heated at reflux overnight. Purification by column chromatography on silica using 3-6% MeOH/CH2Cl2 as the eluent afforded 7-(1-methyl-1-triethylsilanyloxyethyl)-3-[2-(pyridin-4-yl)pyrimidin-4-yl]imidazo[1,2-α]pyrimidine: 1H NMR (400 MHz, d6-DMSO) δ 10.23 (1H, d, J 7.3), 8.98 (1H, d, J 5.4), 8.89 (1H, s), 8.85-8.80 (2H, m), 8.36 (2H, d, J 5.9), 8.14 (1H, d, J 5.5), 7.70 (1H, d, J 7.3), 1.65 (6H, s), 0.95 (9H, t, J 7.8), 0.66 (6H, q, J 7.8).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07030128B2
Source dataset	uspto-grants-2006_04
ORD ID	ord-2bf3af9854a240eb9920608bcb37fdbb
Source note	uspto-grants-2006_04