Methylhydrazine → HCID 83828578, compound

HRID 879638Notes

Reaction equation

HRID 879638 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8](=O)[CH3:9])[C:5](F)=[CH:4][N:3]=1.[CH3:12][NH:13][NH2:14]>C(O)CO.O>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[N:13]([CH3:12])[N:14]=[C:8]([CH3:9])[C:6]=2[N:7]=1

Participants

5

Reactant 2

HCID 6061MethylhydrazineHCID 865947381-(2-Chloro-5-fluoropyrimidin-4-yl)ethanone

Product 1

HCID 83828578HCID 83828578, compound

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 962WaterSolvent

Procedure

A solution of 1-(2-chloro-5-fluoropyrimidin-4-yl)ethanone (4.00 g, 22.91 mmol) and methylhydrazine (0.724 mL, 13.75 mmol) in ethylene glycol was heated at 120° C. for 2 h. Reaction mixture was cooled to rt, diluted with H2O and extracted with ethyl acetate (3×). The combined organic layer was washed with H2O (2×), brine, dried (MgSO4), filtered and concentrated. The residue was purified by CombiFlash (0 to 30% EtOAc/Hex) to give the title compound. LCMS-ESI+: calc'd for C7H8ClN4: 183.0 (M+H+); Found: 183.0 (M+H+); 1H NMR (400 MHz, CDCl3) δ 8.90 (s, 1H), 4.12 (s, 3H), 2.61 (s, 3H).

Workup

  1. customReaction mixture
  2. extractionextracted with ethyl acetate (3×)
  3. washThe combined organic layer was washed with H2O (2×), brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by CombiFlash (0 to 30% EtOAc/Hex)

Sources & evidence

ORD record
ord-5e6f06d2224d4882824aa8b933334d7a
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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