Ethyl 3-oxohexanoate → HCID 135788280, compound

HRID 1822794Notes

Reaction equation

HRID 1822794 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11]([NH2:13])=[NH:12])[CH:2]=1.[C:14]([CH2:19][C:20](OCC)=[O:21])(=O)[CH2:15][CH2:16][CH3:17].[O-]CC.[Na+]>C(O)C>[CH2:15]([C:14]1[N:13]=[C:11]([C:3]2[CH:2]=[N:1][C:10]3[C:5]([CH:4]=2)=[CH:6][CH:7]=[CH:8][CH:9]=3)[NH:12][C:20](=[O:21])[CH:19]=1)[CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 238498Ethyl 3-oxohexanoateHCID 2723922Sodium ethoxideHCID 4572135Quinoline-3-carboximidamide

Product 1

HCID 135788280HCID 135788280, compoundYield 57.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Quinoline-3-carboxamidine (314 mg), ethyl butyrylacetate (290 mg), and sodium ethoxide (21 wt % in ethanol, 1.1 mL) were refluxed for 48 h in 20 mL of ethanol. The solvent was evaporated and the residue was partitioned between ethyl acetate and brine. The ethyl acetate phase was dried with sodium sulfate and the solvent was evaporated. Silica gel chromatography (50:45:5 ethyl acetate/hexanes/methanol) provide 280 mg of 6-propyl-2-quinolin-3-yl-3H-pyrimidin-4-one.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was partitioned between ethyl acetate and brine
  3. dry with materialThe ethyl acetate phase was dried with sodium sulfate
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-c1f9db5231c34998b1a18e9e485bd2bb
Source dataset
uspto-grants-2006_05
Patent number
US07037916B2

Reaction notes

Loading…