HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 5-fluoro-1H-pyrido[2,3-d][1,3]oxazin-2(4H)-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Tert-butyl 3-(bromomethyl)-4-fluoropyridin-2-ylcarbamate | HCID 89656446 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | 5-fluoro-1H-pyrido[2,3-d][1,3]oxazin-2(4H)-one | HCID 89657625 | 30% |
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
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09273046B2 |
| Source dataset | uspto-grants-2016_03 |
| ORD ID | ord-e2d1e44bee204b288941dbbc18a5f565 |
| Source note | uspto-grants-2016_03 |