Acetonitrile → N-{2-[(6-Chloropyrimidin-4-yl)oxy]ethyl}-N-isopropylpropan-2-amine

HRID 2245552Notes

Reaction equation

HRID 2245552 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[CH:9]([N:12]([CH:16]([CH3:18])[CH3:17])[CH2:13][CH2:14][OH:15])([CH3:11])[CH3:10].C(=O)([O-])[O-].[Cs+].[Cs+].C(#N)C>C(#N)CCC>[Cl:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([O:15][CH2:14][CH2:13][N:12]([CH:16]([CH3:18])[CH3:17])[CH:9]([CH3:11])[CH3:10])[CH:7]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 73132-DiisopropylaminoethanolHCID 10796Cesium carbonateHCID 709434,6-Dichloropyrimidine

Product 1

HCID 86624430N-{2-[(6-Chloropyrimidin-4-yl)oxy]ethyl}-N-isopropylpropan-2-amineYield 20.2%

Reagents, catalysts & solvents 1

HCID 8008ButyronitrileSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 4,6-dichloropyrimidine (0.5 g, 3.4 mmol), 2-(diisopropylamino)ethanol (0.44 g, 3.0 mmol), and cesium carbonate (2.18 g, 6.7 mmol) in butyronitrile (4 mL) was heated in a microwave oven at 180° C. for 20 min. Filtration followed by purification using preparative HPLC (XTerra®PrepMS C8 column 10 μm, 30×150 mm; 0.1 M NH4OAc buffer/acetonitrile, (80:20-20:80), as the eluent) gave 0.156 g (20% yield) of the title compound: MS (ESP) m/z 258 (M++1).

Workup

  1. filtrationFiltration
  2. customfollowed by purification

Sources & evidence

ORD record
ord-f447769d7f4848a98d5687c2969a9477
Source dataset
uspto-grants-2010_03
Patent number
US07683067B2

Reaction notes

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