Cesium carbonate → 2-[(1S,2R)-2-{1-[5-(ethoxymethyl)pyrimidin-2-yl]piperidin-4-yl}cyclopropyl]ethanol

HRID 1474703Notes

Reaction equation

Cl[C:2]1[N:7]=[CH:6][C:5]([CH2:8][O:9][CH2:10][CH3:11])=[CH:4][N:3]=1.[NH:12]1[CH2:17][CH2:16][CH:15]([C@H:18]2[CH2:20][C@H:19]2[CH2:21][CH2:22][OH:23])[CH2:14][CH2:13]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O>[CH2:10]([O:9][CH2:8][C:5]1[CH:4]=[N:3][C:2]([N:12]2[CH2:17][CH2:16][CH:15]([C@H:18]3[CH2:20][C@H:19]3[CH2:21][CH2:22][OH:23])[CH2:14][CH2:13]2)=[N:7][CH:6]=1)[CH3:11]

Participants

Conditions

Temperature: 70 °C

Procedure

In a 250 ml RBF 2-chloro-5-(ethoxymethyl)pyrimidine (280 mg, 1.622 mmol) and 2-[(1S,2R)-2-(piperidin-4-yl)cyclopropyl]ethanol (334 mg, 1.622 mmol) were dissolved in DMF (1622 μl). Cesium carbonate (1586 mg, 4.87 mmol) was added and the mixture stirred at 70° C. overnight. The mixture was diluted with 4:1 water:brine (200 ml), extracted with EtOAc (3×100 ml), the organic fractions combined, washed with brine, dried over Na2SO4, filtered and the volatiles removed in vacuo. The mixture was purified on a 100 g Biotage HP-SiO2 cartridge using a gradient eluant of 0-100% EtOAc:hexanes to afford the title compound. LC/MS (m/z): 306 (M+H)+.

Workup

extractionbrine (200 ml), extracted with EtOAc (3×100 ml)
washwashed with brine
dry with materialdried over Na2SO4
filtrationfiltered
customthe volatiles removed in vacuo
customThe mixture was purified on a 100 g Biotage HP-SiO2 cartridge

Sources & evidence

ORD record: ord-cfd3522a902e45c58f938f19cb3fdc9e
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018224B2

Reaction notes

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