2,4-Dichloro-6-methyl-1,3,5-triazine → 2-Chloro-4-(3-(4-chloro-2-fluorophenoxy)azetidin-1-yl)-6-methyl-1,3,5-triazine

HRID 522919Notes

Reaction equation

HRID 522919 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[C:4]([CH3:9])[N:3]=1.CCN(C(C)C)C(C)C.[Cl:19][C:20]1[CH:30]=[CH:29][C:23]([O:24][CH:25]2[CH2:28][NH:27][CH2:26]2)=[C:22]([F:31])[CH:21]=1>C(O)(C)C>[Cl:8][C:6]1[N:7]=[C:2]([N:27]2[CH2:28][CH:25]([O:24][C:23]3[CH:29]=[CH:30][C:20]([Cl:19])=[CH:21][C:22]=3[F:31])[CH2:26]2)[N:3]=[C:4]([CH3:9])[N:5]=1

Participants

5

Reactant 3

HCID 160832,4-Dichloro-6-methyl-1,3,5-triazineHCID 81531DiisopropylethylamineHCID 249023943-(4-Chloro-2-fluorophenoxy)azetidine

Product 1

HCID 866852572-Chloro-4-(3-(4-chloro-2-fluorophenoxy)azetidin-1-yl)-6-methyl-1,3,5-triazineYield 104%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 2,4-dichloro-6-methyl-1,3,5-triazine (0.800 g, 4.87 mmol) in isopropanol (15 mL) was added DIPEA (1.3 mL) and 3-(4-chloro-2-fluorophenoxy)azetidine (0.600 g, 2.92 mmol) and the reaction mixture was stirred at RT for 1 h. The mixture was concentrated under reduced pressure and extracted with EtOAc (2×40 mL). The organic extracts were washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain 2-chloro-4-(3-(4-chloro-2-fluorophenoxy)azetidin-1-yl)-6-methyl-1,3,5-triazine (1.0 g) as a solid. Observed mass (M+1): 329. The crude material was taken to next step without further purification.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. extractionextracted with EtOAc (2×40 mL)
  3. washThe organic extracts were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d6f9e5a6661943048b8e7d60458dab03
Source dataset
uspto-grants-2016_05
Patent number
US09334269B2

Reaction notes

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