Sodium Carbonate → 3-(2-Chlorothieno[3,2-d]pyrimidin-7-yl)benzenamine

https://huagongshe.com/reaction/2042208

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	3-Aminophenylboronic acid	HCID 92269	—
Reactant	Di-tert-butyl(2',4',6'-tris(propan-2-yl)-(1,1'-biphenyl)-2-yl)phosphane	HCID 11618717	—
Reactant	7-Bromo-2-chlorothieno(3,2-d)pyrimidine	HCID 56965724	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	3-(2-Chlorothieno[3,2-d]pyrimidin-7-yl)benzenamine	HCID 86673214	73.2%

Reaction Conditions

Temperature	90 °C

Reaction Steps

7-Bromo-2-chlorothieno[3,2-d]pyrimidine (3.645 g, 14.61 mmol) was dissolved in dioxane (44 mL) and 2.0 N sodium carbonate (22 mL, 43.83 mmol) and 3-aminophenylboronic acid (2 g, 14.61 mmol) were added. After flowing nitrogen to the mixture solution for 10 minutes, Pd2(PPh3)Cl2 (615 mg, 0.88 mmol) and t-ButylXphos (558 mg, mmol) were added. The reaction mixture solution was stirred at 90° C. for 6 hours and filtered with celite. The filtrate was diluted with ethyl acetate and washed with brine. The organic layer was concentrated by drying with magnesium sulfate. Purification by chromatography (20% ethyl acetate/hexane) yielded the target compound (2.8 g, 73% yield).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08586580B2
Source dataset	uspto-grants-2013_11
ORD ID	ord-ef7788220f304c0fac7e0b4d7d0882f0
Source note	uspto-grants-2013_11