Triethylamine → ethyl (R)-2-(3-(2-ethoxyphenoxy)piperidin-1-yl)pyrimidine-5-carboxylate

HRID 59886Notes

Reaction equation

[CH2:1]([O:3][C:4]1[CH:16]=[CH:15][CH:14]=[CH:13][C:5]=1[O:6][C@@H:7]1[CH2:12][CH2:11][CH2:10][NH:9][CH2:8]1)[CH3:2].Cl[C:18]1[N:23]=[CH:22][C:21]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:20][N:19]=1.CCN(CC)CC>CS(C)=O.O>[CH2:1]([O:3][C:4]1[CH:16]=[CH:15][CH:14]=[CH:13][C:5]=1[O:6][C@@H:7]1[CH2:12][CH2:11][CH2:10][N:9]([C:18]2[N:19]=[CH:20][C:21]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:22][N:23]=2)[CH2:8]1)[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of (R)-3-(2-ethoxyphenoxy)piperidine (45 g, 204 mmol) and ethyl 2-chloropyrimidine-5-carboxylate (41.7 g, 224 mmol) in DMSO (300 mL) was added Et3N (40 mL, 305 mmol) at 20-25° C. The reaction mixture was heated to 100° C. for 2 hours, then was cooled to 20-25° C., diluted with H2O (300 mL) and extracted with EtOAc (3 times with 300 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated to obtain ethyl (R)-2-(3-(2-ethoxyphenoxy)piperidin-1-yl)pyrimidine-5-carboxylate (71.5 g). MS (ES+) 372.3 (M+H).

Workup

temperaturewas cooled to 20-25° C.
extractionextracted with EtOAc (3 times with 300 mL)
dry with materialThe combined organic extracts were dried over Na2SO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-a50cd4e48aab4bf8adab0c49ee32b56a
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440949B2

Reaction notes

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