Sodium Carbonate → 2-chloro-4-(2-fluoropyridin-4-yl)pyrimidine

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	2,4-Dichloropyrimidine	HCID 77531	—
Reactant	2-Fluoropyridine-4-boronic acid	HCID 2783396	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Water	HCID 962	—
Solvent	1,4-Dioxane--water (1/1)	HCID 21886435	—
Product	2-chloro-4-(2-fluoropyridin-4-yl)pyrimidine	HCID 640536	96.8%

Reaction Conditions

Temperature	80 °C

Reaction Steps

Sodium carbonate (4.91 g, 46.3 mmol) was added to 2-fluoropyridin-4-ylboronic acid (2.61 g, 18.5 mmol) and 2,4-dichloropyrimidine (77.2 mL, 15.4 mmol) in dioxane/water (77 mL, 4:1), and the suspension was purged with argon. PdCl2(dppf)*DCM (0.630 g, 0.772 mmol) was added to the mixture, and the mixture was heated at 80° C. under argon. After 3 hours, the reaction mixture was diluted with water, and the resulting solid was collected by vacuum filtration to yield 2-chloro-4-(2-fluoropyridin-4-yl)pyrimidine (3.12 g, 14.9 mmol, 96.4% yield) with minor impurities.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09259470B2
Source dataset	uspto-grants-2016_02
ORD ID	ord-9c5764f03de44ad2831e29fab91c5845
Source note	uspto-grants-2016_02