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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1524151Generated: November 2, 2026

Thionyl Chloride → 5-(6'-(Chloromethyl)-3-fluorobiphenyl-4-yl)pyrazin-2-amine

https://huagongshe.com/reaction/1524151

Reaction equation

Participants

RoleNameHCIDCharge
ReactantThionyl ChlorideHCID 24386—
Reactant(4'-(5-Aminopyrazin-2-yl)-5'-fluorobiphenyl-2-yl)methanolHCID 90313341—
SolventDichloromethaneHCID 6344—
Product5-(6'-(Chloromethyl)-3-fluorobiphenyl-4-yl)pyrazin-2-amineHCID 9031294498%

Reaction Conditions

Temperature70 °C

Reaction Steps

A mixture of (4′-(5-aminopyrazin-2-yl)-3′-fluoro-[1,1′-biphenyl]-2-yl)methanol (1.8 g, 6.1 mmol) and SOCl2 (6 mL) in DCM (20 mL) was stirred at 70° C. for 4 h. The reaction mixture was cooled to rt and concentrated to dryness to give the title compound (1.86 g, 98%). 1H NMR (300 MHz, DMSO-d6) δ 8.40 (s, 1H), 8.04 (s, 1H), 7.96 (m, 1H), 7.66-7.57 (m, 1H), 7.51-7.42 (m, 2H), 7.40-7.30 (m, 3H), 6.89-6.62 (m, 2H), 4.73 (s, 2H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09079866B2
Source datasetuspto-grants-2015_07
ORD IDord-f7a0bda6fb7e456c9bf2ffce774aa3f2
Source noteuspto-grants-2015_07