Water → 4-(Azetidin-1-yl)-2-chloro-6-((2,2,2-trifluoroethoxy)methyl)pyrimidine

HRID 59114Notes

Reaction equation

[NH:1]1[CH2:4][CH2:3][CH2:2]1.C[O-].[Na+].[Cl:8][C:9]1[N:14]=[C:13](Cl)[CH:12]=[C:11]([CH2:16][O:17][CH2:18][C:19]([F:22])([F:21])[F:20])[N:10]=1.O>CO.C(#N)C>[N:1]1([C:13]2[CH:12]=[C:11]([CH2:16][O:17][CH2:18][C:19]([F:22])([F:21])[F:20])[N:10]=[C:9]([Cl:8])[N:14]=2)[CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of azetidine (0.224 g, 2.39 mmol) and sodium methoxide (0.326 mL, 1.75 mmol) in MeOH (2 mL) was added to an ice-cold solution of 2,4-dichloro-6-((2,2,2-trifluoroethoxy)-methyl)pyrimidine (0.208 g, 0.80 mmol) in acetonitrile (2 mL). The mixture was stirred at 0° C. for 15 minutes. Water was added. The mixture was purified by preparative HPLC to give the title compound, 0.091 g (41%).

Workup

customThe mixture was purified by preparative HPLC

Sources & evidence

ORD record: ord-7cca4d8138f842bb8432c4161ece299f
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09439904B2

Reaction notes

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