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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 920127Generated: October 26, 2026

Water → 5-fluoro-1H-pyrido[2,3-d][1,3]oxazin-2(4H)-one

https://huagongshe.com/reaction/920127

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantTert-butyl 3-(bromomethyl)-4-fluoropyridin-2-ylcarbamateHCID 89656446—
SolventDimethyl SulfoxideHCID 679—
Product5-fluoro-1H-pyrido[2,3-d][1,3]oxazin-2(4H)-oneHCID 8965762530%

Reaction Steps

The solution of the product of Step C (120 mg, 0.4 mmol) in DMSO (1 mL) was stirred at 60° C. for 4 hours under N2. Then water (10 mL) was added and extracted with ethyl acetate (3×15 mL). The combined organic phase was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by prep-TLC (EtOAc:PE=1:1) to give the title compound (20 mg, 30%) as a solid. 1H-NMR (600 MHz, DMSO-d6) δ 10.95 (s, 1H), 8.21-8.18 (m, 1H), 6.97-6.94 (m, 1H), 5.37 (s, 2H) ppm. MS: M/e 169 (M+1)+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09273046B2
Source datasetuspto-grants-2016_03
ORD IDord-e2d1e44bee204b288941dbbc18a5f565
Source noteuspto-grants-2016_03