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

HRID 522894Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.C(N(C(C)C)C(C)C)C.Cl.[F:19][C:20]1[CH:30]=[CH:29][C:23]([O:24][CH:25]2[CH2:28][NH:27][CH2:26]2)=[CH:22][CH:21]=1>CC(O)C>[Cl:1][C:2]1[N:7]=[C:6]([N:27]2[CH2:28][CH:25]([O:24][C:23]3[CH:22]=[CH:21][C:20]([F:19])=[CH:30][CH:29]=3)[CH2:26]2)[CH:5]=[CH:4][N:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To 2,4-dichloropyrimidine (200.0 mg, 1.342 mmol) in 2-propanol (7 mL) at 0° C. was added N-ethyl-N-isopropylpropan-2-amine (0.702 mL, 4.03 mmol) followed by 3-(4-fluorophenoxy)azetidine hydrochloride (273 mg, 1.342 mmol). The resulting reaction mixture was stirred at 0° C. for 10 min then at RT for 41 h and concentrated. Purification of the crude product was done using MPLC (25 g cartridge, 40 g column, 0 to 60% EtOAc-hexanes) to give 2-chloro-4-(3-(4-fluorophenoxy)azetidin-1-yl)pyrimidine (314.2 mg).

Workup

customThe resulting reaction mixture
waitat RT for 41 h
concentrationconcentrated
customPurification of the crude product

Sources & evidence

ORD record: ord-dccf79d6a0e74c7b9c02bc14fdfccd58
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09334269B2

Reaction notes

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