2,4-Dichloro-1,3,5-triazine → 2-Chloro-4-(3-(4-chloro-2-fluorophenoxy)azetidin-1-yl)-1,3,5-triazine

HRID 522908Notes

Reaction equation

HRID 522908 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][CH:7]2[CH2:10][NH:9][CH2:8]2)=[C:4]([F:13])[CH:3]=1.[Cl:14][C:15]1[N:20]=[C:19](Cl)[N:18]=[CH:17][N:16]=1>C(#N)C>[Cl:14][C:15]1[N:20]=[C:19]([N:9]2[CH2:10][CH:7]([O:6][C:5]3[CH:11]=[CH:12][C:2]([Cl:1])=[CH:3][C:4]=3[F:13])[CH2:8]2)[N:18]=[CH:17][N:16]=1

Participants

4

Reactant 2

HCID 178102,4-Dichloro-1,3,5-triazineHCID 249023943-(4-Chloro-2-fluorophenoxy)azetidine

Product 1

HCID 866852562-Chloro-4-(3-(4-chloro-2-fluorophenoxy)azetidin-1-yl)-1,3,5-triazineYield 20%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-(4-chloro-2-fluorophenoxy) azetidine (3.6 g, 18.0 mmol) in acetonitrile (60 mL, 3 mL/mmol) was added TEA (7.2 mL, 50.0 mmol) and 2, 4-dichloro-1, 3, 5-triazine (3.0 g, 20.0 mmol) and the reaction mixture was stirred at RT for 1 h. The reaction mixture was concentrated under reduced pressure and extracted with EtOAc (2×50 mL). The organic extracts were washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification by silica gel column chromatography provided 2-chloro-4-(3-(4-chloro-2-fluorophenoxy)azetidin-1-yl)-1,3,5-triazine (0.800 g, 20%) as a solid. Observed mass (M+1): 315.0

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionextracted with EtOAc (2×50 mL)
  3. washThe organic extracts were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customPurification by silica gel column chromatography

Sources & evidence

ORD record
ord-8a3d6d866e304513805f85685a5cb9a7
Source dataset
uspto-grants-2016_05
Patent number
US09334269B2

Reaction notes

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