Sodium hydride → tert-Butyl 4-{[6-chloro-2-(trifluoromethyl)pyrimidin-4-yl]oxy}piperidine-1-carboxylate

HRID 1426352Notes

Reaction equation

[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[Cl:15][C:16]1[CH:21]=[C:20](Cl)[N:19]=[C:18]([C:23]([F:26])([F:25])[F:24])[N:17]=1.[H-].[Na+]>C1COCC1>[Cl:15][C:16]1[N:17]=[C:18]([C:23]([F:26])([F:25])[F:24])[N:19]=[C:20]([O:1][CH:2]2[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]2)[CH:21]=1

Participants

Conditions

Temperature: 0 °C

Procedure

In a reaction flask, tert-butyl 4-hydroxypiperidine-1-carboxylate (2.02 g, 10.0 mmol) and 4,6-dichloro-2-(trifluoromethyl)pyrimidine (2.18 g, 10.0 mmol) were dissolved in THF (19.7 mL) and cooled to 0° C. Sodium hydride (0.603 g, 15.1 mmol) was added and then the mixture was stirred for 30 minutes at 0° C. and at 25° C. for another 16 hours. The reaction was quenched with water, and was extracted with ethyl acetate and the organic extracts were washed with water, brine, dried over MgSC4, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography to give the product.

Workup

customThe reaction was quenched with water
extractionwas extracted with ethyl acetate
washthe organic extracts were washed with water, brine
dry with materialdried over MgSC4
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by silica gel chromatography
customto give the product

Sources & evidence

ORD record: ord-f2b37a3b79c242f98bd1c74c40c5616f
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08933085B2

Reaction notes

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