Hydrochloric Acid → HCID 25104492, compound

Participants

Role	Name	HCID	Charge
Reactant	Hydrochloric Acid	HCID 313	—
Reactant	Sodium Bicarbonate	HCID 516892	—
Reactant	HCID 57498047	HCID 57498047	—
Reactant	(2-Oxo-2,3-dihydro-1,3-benzoxazol-6-yl)boronic acid	HCID 59348976	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	HCID 25104492	HCID 25104492	—

Reaction Conditions

Temperature	70 °C

Reaction Steps

A round flask was charged with 2,4-dichloro-6-(2-chlorophenyl)pyrimidine (150 mg), 2-oxo-2,3-dihydrobenzo[d]oxazol-6-ylboronic acid (104 mg), Pd(dppf)Cl2(15 mg), 1 M NaHCO3 (0.5 mL) and THF (5 mL). The reaction mixture was stirred at 70° C. for 2 hours, then 4 mL of conc. HCl was added. The reaction was heated to 90° C. for 5 hours. The mixture was filtrated, concentrated and purified by prep-HPLC to give the product. 1H NMR (400 MHz, d6-DMSO): δ 11.00 (s, br, 2H), 7.81-7.75 (m, 2H), 7.62-7.43 (m, 3H), 7.12-7.00 (m, 3H). MS (EI) for C17H10ClN3O3: 339 (MH+).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08242129B2
Source dataset	uspto-grants-2012_08
ORD ID	ord-05524fce01dc49d6b28a73a2ab975ebf
Source note	uspto-grants-2012_08