(Z)-Benzaldehyde oxime → HCID 75985010, compound

HRID 1403179Notes

Reaction equation

HRID 1403179 reaction equation
[H-].[Na+].[CH:3](=[N:10][OH:11])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[F:12][C:13]1[C:14]([N:23]=[CH:24][N:25]([CH3:27])[CH3:26])=[N:15][C:16](S(C)(=O)=O)=[N:17][CH:18]=1>CN(C=O)C.O>[F:12][C:13]1[C:14]([N:23]=[CH:24][N:25]([CH3:27])[CH3:26])=[N:15][C:16]([O:11][N:10]=[CH:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[N:17][CH:18]=1

Participants

6

Reactant 3

HCID 12143(Z)-Benzaldehyde oximeHCID 24758Sodium hydrideHCID 58318919HCID 58318919, compound

Product 1

HCID 75985010HCID 75985010, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent3×

Procedure

To a suspension of sodium hydride (NaH, 60% dispersion in mineral oil; 0.037 g, 0.91 mmol) in DMF (2 mL) was added a solution of benzaldehyde oxime (0.125 g, 1.04 mmol) in DMF (1 mL), and the resulting frothy mixture was stirred for 1 h. To the resulting pale yellow mixture was added a solution of N′-(5-fluoro-2-methanesulfonylpyrimidin-4-yl)-N,N-dimethylformamidine (0.15 g, 0.61 mmol) in DMF (1 mL), and the homogeneous, pale-yellow solution was stirred at 25° C. for 16 h. The reaction mixture was diluted with H2O (50 mL) and was extracted with CH2Cl2 (2×100 mL). The organic extracts were combined, washed with H2O (5×50 mL) and brine (50 mL), dried over Na2SO4, filtered, and concentrated to a colorless oil. Trituration with Et2O afforded N′-{5-fluoro-2-[1-phenylmethylideneaminooxy]pyrimidin-4-yl}-N,N-dimethylformamidine (0.054 g, 31%) as a white solid: mp 240-244° C. dec; 1H NMR (400 MHz, CDCl3) δ 8.73 (s, 1H), 8.53 (s, 1H), 8.19 (d, J=2.4 Hz, 1H), 7.81-7.69 (m, 2H), 7.49-7.30 (m, 3H), 3.21 (s, 3H), 3.21 (s, 3H); ESIMS m/z 288 ([M+H]+).

Workup

  1. stirringthe homogeneous, pale-yellow solution was stirred at 25° C. for 16 h
  2. extractionwas extracted with CH2Cl2 (2×100 mL)
  3. washwashed with H2O (5×50 mL) and brine (50 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to a colorless oil

Sources & evidence

ORD record
ord-f478484003d0433fbb7db105cb8cd837
Source dataset
uspto-grants-2014_12
Patent number
US08912207B2

Reaction notes

Loading…