Dichloromethane → 4-[6-[(3R)-3-Ethyl-4-morpholinyl]-2-(methylamino)-4-pyrimidinyl]-2-fluorobenzonitrile

Participants

Role	Name	HCID	Charge
Reactant	Dichloromethane	HCID 6344	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	(4-Cyano-3-fluorophenyl)boronic acid	HCID 2783130	—
Reactant	HCID 58504396	HCID 58504396	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	4-[6-[(3R)-3-Ethyl-4-morpholinyl]-2-(methylamino)-4-pyrimidinyl]-2-fluorobenzonitrile	HCID 58504763	139.5%

Reaction Conditions

Temperature	140 °C

Reaction Steps

4-Chloro-6-[(3R)-3-ethyl-4-morpholinyl]-N-methyl-2-pyrimidinamine (250 mg, 0.974 mmol) was added to a 20 mL microwave vial, followed by (4-cyano-3-fluorophenyl)boronic acid (209 mg, 1.266 mmol), PdCl2(dppf).CH2Cl2 adduct (39.8 mg, 0.049 mmol), 2M K2CO3 (1.461 mL, 2.92 mmol) and 1,4-dioxane (4 mL). The mixture was heated to 140° C. for 10 minutes. The reaction mixture was filtered through a silica plug and washed with EtOAc (3×). The filtrate was then washed with H2O (2×) and the organic layer was dried over Na2SO4 and concentrated to afford the title compound (464 mg) as a brown oil. LC-MS (ES) m/z=342 [M+H]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08697685B2
Source dataset	uspto-grants-2014_04
ORD ID	ord-c1897c49e08c4fd692a5d7870e99b317
Source note	uspto-grants-2014_04