Cesium carbonate → HCID 89581860, compound

HRID 1474719Notes

Reaction equation

HRID 1474719 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 volatiles evaporated under reduced pressure. The crude material was purified by silica gel column chromatography (100 g SNAP, 20˜60% EtOAc in hexane) to afford the titled compound. 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. customthe volatiles evaporated under reduced pressure
  5. customThe crude material was purified by silica gel column chromatography (100 g SNAP, 20˜60% EtOAc in hexane)

Sources & evidence

ORD record
ord-3ca39b6fae35465bb9488bfca814bb00
Source dataset
uspto-grants-2015_04
Patent number
US09018224B2

Reaction notes

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