Propanal, 2-methyl-, oxime → HCID 76759416, compound

HRID 1403186Notes

Reaction equation

HRID 1403186 reaction equation
[CH3:1][CH:2]([CH3:6])[CH:3]=[N:4][OH:5].CC(C)([O-])C.[K+].[F:13][C:14]1[CH:32]=[CH:31][CH:30]=[CH:29][C:15]=1[CH2:16][NH:17][C:18]1[C:23]([F:24])=[CH:22][N:21]=[C:20](S(C)(=O)=O)[N:19]=1>C1COCC1>[F:24][C:23]1[C:18]([NH:17][CH2:16][C:15]2[CH:29]=[CH:30][CH:31]=[CH:32][C:14]=2[F:13])=[N:19][C:20]([O:5][N:4]=[CH:3][CH:2]([CH3:6])[CH3:1])=[N:21][CH:22]=1

Participants

5

Reactant 3

HCID 9023Propanal, 2-methyl-, oximeHCID 23665647Potassium tert-butoxideHCID 58318937HCID 58318937, compound

Product 1

HCID 76759416HCID 76759416, compoundYield 551.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-methylpropionaldehyde oxime (0.047 g, 0.54 mmol) in anhydrous THF (3 mL) was added a solution of potassium tert-butoxide (KOtBu, 1 M in THF; 0.50 mL, 0.50 mmol) at room temperature, and the resulting pale-yellow mixture was stirred for 15 min. To the resulting solution was added 2-fluorobenzyl-(5-fluoro-2-methanesulfonylpyrimidin-4-yl)amine (0.125 g, 0.42 mmol), and the resulting tan mixture was stirred at room temperature for 16 h. The entire reaction mixture was adsorbed to Celite (2.5 g) and the adsorbed material was purified by flash chromatography (40 g SiO2; 0→100% EtOAc/hexanes) to give 2-methylpropionaldehyde O-[5-fluoro-4-(2-fluorobenzylamino)-pyrimidin-2-yl]oxime (0.71 g, 56%) as a colorless oil: IR (thin film) 3261, 3179, 3049, 2973, 2936, 2872, 1676, 1622, 1568, 1531, 1491, 1457, 1409, 1372 cm−1; 1H NMR (400 MHz, CDCl3) δ 7.91 (d, J=2.5 Hz, 1H), 7.71 (d, J=7.5 Hz, 1H), 7.43 (t, J=6.9 Hz, 1H), 7.29 (m, J=7.6 Hz, 1H), 7.09 (m, 2H), 5.42 (s, 1H), 4.76 (d, J=5.8 Hz, 2H), 2.79 (dq, J=13.9, 6.9 Hz, 1H), 1.18 (d, J=6.8 Hz, 6H); ESIMS m/z 307 ([M+H]+), 305 ([M−H]−).

Workup

  1. stirringthe resulting tan mixture was stirred at room temperature for 16 h
  2. customThe entire reaction mixture
  3. customthe adsorbed material was purified by flash chromatography (40 g SiO2; 0→100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-7613eec9c1134ac9b61e609264e445c0
Source dataset
uspto-grants-2014_12
Patent number
US08912207B2

Reaction notes

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