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

HRID 920127Notes

Reaction equation

HRID 920127 reaction equation
BrC[C:3]1[C:4]([NH:10][C:11](=[O:17])[O:12][C:13](C)(C)C)=[N:5][CH:6]=[CH:7][C:8]=1[F:9].O>CS(C)=O>[F:9][C:8]1[C:3]2[CH2:13][O:12][C:11](=[O:17])[NH:10][C:4]=2[N:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 962WaterHCID 89656446Tert-butyl 3-(bromomethyl)-4-fluoropyridin-2-ylcarbamate

Product 1

HCID 896576255-fluoro-1H-pyrido[2,3-d][1,3]oxazin-2(4H)-oneYield 30%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

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)+.

Workup

  1. extractionextracted with ethyl acetate (3×15 mL)
  2. washThe combined organic phase was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by prep-TLC (EtOAc:PE=1:1)

Sources & evidence

ORD record
ord-e2d1e44bee204b288941dbbc18a5f565
Source dataset
uspto-grants-2016_03
Patent number
US09273046B2

Reaction notes

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