Dichloromethane → Tert-butyl 4-(5-chloropyrimidin-2-yl)benzylcarbamate

Participants

Role	Name	HCID	Charge
Reactant	Dichloromethane	HCID 6344	—
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	2,5-Dichloropyrimidine	HCID 590641	—
Reactant	4-(tert-Butoxycarbonylaminomethyl)phenylboronic acid	HCID 3863163	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	Tert-butyl 4-(5-chloropyrimidin-2-yl)benzylcarbamate	HCID 90410805	70.4%

Reaction Conditions

Temperature	80 °C

Reaction Steps

To a 10 mL microwave vial were added 2,5-dichloropyrimidine (285 mg, 1.8 mmol), Pd(dppf)Cl2.DCM (45 mg, 0.05 mmol), (4-(((tert-butoxycarbonyl)amino)methyl)phenyl)boronic acid (419 mg, 1.67 mmol), Na2CO3 (2 mL, 2M) and 1,4-dioxane (7 mL). The vial was flushed with N2 then capped and placed in a heating block and heated at 80° Celsius. After 6 h, the resulting mixture cooled to RT and transferred to a round-bottomed flask and concentrated to dryness. The residue was purified using FCC to provide 376 mg of the title compound. MS (ESI): mass calcd. for C16H18ClN3O2, 319.11; m/z found 320.1 [M+H]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08952177B2
Source dataset	uspto-grants-2015_02
ORD ID	ord-21e6ddde78e740d5afc5162e6302a285
Source note	uspto-grants-2015_02