Dimethylformamide dimethyl acetal → HCID 76759378, compound

HRID 1403183Notes

Reaction equation

HRID 1403183 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[CH:6][N:5]=[C:4]([O:9][N:10]=[CH:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[N:3]=1.[CH3:20][N:21]([CH:23](OC)OC)[CH3:22]>CN(C=O)C.CCOCC>[F:8][C:7]1[C:2]([N:1]=[CH:20][N:21]([CH3:23])[CH3:22])=[N:3][C:4]([O:9][N:10]=[CH:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[N:5][CH:6]=1

Participants

5

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 76759402HCID 76759402, compound

Product 1

HCID 76759378HCID 76759378, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a magnetically stirred suspension of 4-methoxybenzaldehyde O-(4-amino-5-fluoropyrimidin-2-yl)oxime (0.075 g, 0.29 mmol) in anhydrous DMF (0.2 mL) was added DMF-DMA (0.068 g, 0.57 mmol) and the resulting mixture was stirred at room temperature for 3 h. The reaction mixture was diluted with Et2O (10 mL) and then was cooled to 0° C. The resulting solid was collected by vacuum filtration, and the cake was washed with cold Et2O followed by hexanes. The precipitate that formed in the filtrate was collected by vacuum filtration and the combined solids were dried under vacuum to give N′-{5-fluoro-2-[1-(4-methoxyphenyl)-methylideneaminooxy]pyrimidin-4-yl}-N,N-dimethylformamidine (0.069 g, 76%) as a white solid: mp 243-245° C. dec; 1H NMR (300 MHz, DMSO-d6) δ 8.68 (s, 1H), 8.60 (s, 1H), 8.26 (d, J=2.7 Hz, 1H), 7.73 (d, J=8.6 Hz, 2H), 7.05 (d, J=8.6 Hz, 2H), 3.82 (s, 3H), 3.21 (s, 3H), 3.10 (s, 3H); ESIMS m/z 318 ([M+H]+).

Workup

  1. temperaturewas cooled to 0° C
  2. filtrationThe resulting solid was collected by vacuum filtration
  3. washthe cake was washed with cold Et2O
  4. customThe precipitate that formed in the filtrate
  5. filtrationwas collected by vacuum filtration
  6. customthe combined solids were dried under vacuum

Sources & evidence

ORD record
ord-4aa0be019141495f91b70d0d4dda5102
Source dataset
uspto-grants-2014_12
Patent number
US08912207B2

Reaction notes

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