m-Chloroperbenzoic acid → 4-(5-(3,3-Dimethyloxiran-2-YL)-2-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-YL)-6-methyl-1,3,5-triazin-2-amine

HRID 1621985Notes

Reaction equation

HRID 1621985 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[C:16]([C:17]3[N:22]=[C:21]([CH3:23])[N:20]=[C:19]([NH2:24])[N:18]=3)=[CH:15][C:14]([CH:25]=[C:26]([CH3:28])[CH3:27])=[CH:13][N:12]=2)[CH:5]=[N:6][C:7]=1[O:8][CH3:9].ClC1C=C(C=CC=1)C(OO)=[O:34]>C(Cl)Cl.CCOC(C)=O>[CH3:27][C:26]1([CH3:28])[O:34][CH:25]1[C:14]1[CH:15]=[C:16]([C:17]2[N:22]=[C:21]([CH3:23])[N:20]=[C:19]([NH2:24])[N:18]=2)[C:11]([NH:10][C:4]2[CH:5]=[N:6][C:7]([O:8][CH3:9])=[C:2]([F:1])[CH:3]=2)=[N:12][CH:13]=1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 666121544-(2-(5-Fluoro-6-methoxypyridin-3-ylamino)-5-(2-methylprop-1-enyl)pyridin-3-YL)-6-methyl-1,3,5-triazin-2-amine

Product 1

HCID 866470834-(5-(3,3-Dimethyloxiran-2-YL)-2-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-YL)-6-methyl-1,3,5-triazin-2-amine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 4-(2-(5-fluoro-6-methoxypyridin-3-ylamino)-5-(2-methylprop-1-enyl)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine (380 mg, 0.996 mmol) in DCM (9.9 mL) was cooled to 0° C., and 3-chlorobenzoperoxoic acid (268 mg, 1.196 mmol) was then added. The resulting mixture was stirred at 0° C. for 1.5 h and then allowed to warm to ambient temperature and stir for 2 h. The reaction mixture was then diluted with 200 mL of EtOAc, added to a separatory funnel and partitioned with sodium bicarbonate (saturated, aqueous). The organic layer was washed 1 time with 150 mL of sodium bicarbonate (saturated, aqueous), separated, dried over sodium sulfate, and concentrated in vacuo to give the title compound. m/z (ESI, +ve ion) 398.2 (M+H)+.

Workup

  1. temperatureto warm to ambient temperature
  2. stirringstir for 2 h
  3. additionadded to a separatory funnel
  4. custompartitioned with sodium bicarbonate (saturated, aqueous)
  5. washThe organic layer was washed 1 time with 150 mL of sodium bicarbonate (saturated, aqueous)
  6. customseparated
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-31db7a14f9894744bfc6499cc8febb14
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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