1,4-Dioxane → 4-(2-Chloro-7-vinylthieno[3,2-d]pyrimidin-4-yl)morpholine

Participants

Role	Name	HCID	Charge
Reactant	1,4-Dioxane	HCID 31275	—
Reactant	7-Bromo-2-chloro-4-(4-morpholinyl)-thieno[3,2-d]pyrimidine	HCID 53438708	—
Catalyst	HCID 178418397	HCID 178418397	—
Product	4-(2-Chloro-7-vinylthieno[3,2-d]pyrimidin-4-yl)morpholine	HCID 70676605	39.5%

Reaction Conditions

Temperature	100 °C

Reaction Steps

4-(7-bromo-2-chlorothieno[3,2-d]pyrimidin-4-yl)morpholine (3.55 g, 10.6 mmol), (2-Ethenyl)tri-n-butyltin (3.41 mL, 11.7 mmol), Pd(PPh3)4 (613 mg, 0.53 mmol), and 1,4-Dioxane (30 mL, 400 mmol) were combined in a sealed tube and heated at 100° C. 19.5 h. Complete reaction was confirmed by LCMS. Concentrated in vacuo and purified by silica gel chromatography (0 to 50% ethyl acetate/heptanes) on the CombiFlash® Rf system and concentrated in vacuo to give 4-(2-chloro-7-vinylthieno[3,2-d]pyrimidin-4-yl)morpholine (1.18 g, 39.5% yield)

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08883799B2
Source dataset	uspto-grants-2014_11
ORD ID	ord-478cbca551254b3482e017c4823894d9
Source note	uspto-grants-2014_11