2,4-Dichloropyrimidine → 2-Chloro-4-(3-(2,4-dichlorophenoxy)azetidin-1-yl)pyrimidine

HRID 522906Notes

Reaction equation

[Cl:1][C:2]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:3]=1[O:4][CH:5]1[CH2:8][NH:7][CH2:6]1.C(N(CC)C(C)C)(C)C.[Cl:23][C:24]1[N:29]=[C:28](Cl)[CH:27]=[CH:26][N:25]=1>C(O)(C)C>[Cl:23][C:24]1[N:29]=[C:28]([N:7]2[CH2:8][CH:5]([O:4][C:3]3[CH:9]=[CH:10][C:11]([Cl:13])=[CH:12][C:2]=3[Cl:1])[CH2:6]2)[CH:27]=[CH:26][N:25]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 3-(2,4-dichlorophenoxy)azetidine (1.0 g, 4.6 mmol) in isopropanol (14 mL) was added N,N-diisopropylethylamine (DIPEA) (1.0 mL, 6.9 mmol) and 2,4-dichloropyrimidine (0.686 g, 4.6 mmol and the reaction mixture was heated at 80° C. for 7 h. The mixture was concentrated under reduced pressure and extracted with EtOAc (2×20 mL) and water (2×20 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-(2,4-dichlorophenoxy)azetidin-1-yl)pyrimidine (0.600 g, 40%) as a solid. Observed mass (M+1): 330.0

Workup

concentrationThe mixture was concentrated under reduced pressure
extractionextracted with EtOAc (2×20 mL) and water (2×20 mL)
washThe organic extracts were washed with brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customPurification by silica gel column chromatography

Sources & evidence

ORD record: ord-a2c8af248ac64a929566667eaf8a52d2
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09334269B2

Reaction notes

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