Cesium carbonate → HCID 89581860, compound

HRID 1474692Notes

Reaction equation

HRID 1474692 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C@H:7]2[CH2:9][C@H:8]2[CH2:10][CH2:11][OH:12])[CH2:3][CH2:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:20]1[N:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][N:21]=1>CN(C=O)C.CCOC(C)=O>[CH3:27][O:26][C:23]1[CH:22]=[N:21][C:20]([N:1]2[CH2:6][CH2:5][CH:4]([C@H:7]3[CH2:9][C@H:8]3[CH2:10][CH2:11][OH:12])[CH2:3][CH2:2]2)=[N:25][CH:24]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 5890582-Chloro-5-methoxypyrimidineHCID 867111782-((1S,2R)-2-(piperidin-4-yl)cyclopropyl)ethanol

Product 1

HCID 89581860HCID 89581860, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-((1S,2R)-2-(Piperidin-4-yl)cyclopropyl)ethanol (2.5 g, 14.77 mmol) was dissolved in DMF (30 ml) at RT under N2 and cesium carbonate (7.22 g, 22.15 mmol) was added. The mixture was stirred at RT for 5 min and 2-chloro-5-methoxypyrimidine (2.56 g, 17.72 mmol) was added. The mixture was stirred at 100° C. overnight. The mixture was diluted with EtOAc (100 ml), washed with sat. NH4Cl (100 ml), dried over MgSO4, and the concentrated in vacuo. The crude material was purified by silica gel column (100 g SNAP, 2060% EtOAc in hexane) to afford the title compound as a white solid. LC/MS (m/z): 278 (M+H)+. Rf was 0.4 @ 50% EtOAc in hexanes (blue spot on CAM stain).

Workup

  1. stirringThe mixture was stirred at 100° C. overnight
  2. washwashed with sat. NH4Cl (100 ml)
  3. dry with materialdried over MgSO4
  4. concentrationthe concentrated in vacuo
  5. customThe crude material was purified by silica gel column (100 g SNAP, 2060% EtOAc in hexane)

Sources & evidence

ORD record
ord-b68b0e1702354c02ad56628fbbafeb13
Source dataset
uspto-grants-2015_04
Patent number
US09018224B2

Reaction notes

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