Potassium Carbonate → HCID 85873129, compound

HRID 2245551Notes

Reaction equation

HRID 2245551 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[OH:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([O:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 611632-MorpholinoethanolHCID 709434,6-Dichloropyrimidine

Product 1

HCID 85873129HCID 85873129, compoundYield 321.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4,6-dichloropyrimidine (1.0 g, 6.7 mmol), N-(2-hydroxyethyl)morpholine (0.79 g, 0.60 mmol), and potassium carbonate (2.8 g, 20 mmol) in acetonitrile (5 mL) was stirred at room temperature for 15 h. The solvent was removed in vacuo and the residue was purified on a silica gel column using a gradient dichloromethane/methanol, (100:1 to 2:1), as the eluent to give 0.47 g (32% yield) of the yellow title compound: 1H NMR (CDCl3, 400 MHz) δ 8.48 (s, 1H), 6.72 (s, 1H), 4.45 (t, J=6 Hz, 2H), 3.62 (m, 4H), 2.46 (m, 4H) 2.69 (t, J=6 Hz, 2H), 13C NMR (CDCl3, 100 MHz) δ 169.9, 160.5, 157.9, 107.8, 66.7, 64.4; MS (ESP) m/z 244 (M++1).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-7b15dd65435946c09b200ebd573f0203
Source dataset
uspto-grants-2010_03
Patent number
US07683067B2

Reaction notes

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