Methyl 3-oxoheptanoate → HCID 135788278, compound

HRID 1822777Notes

Reaction equation

HRID 1822777 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH2:7])=[NH:6].C[O:12][C:13](=O)[CH2:14][C:15](=O)[CH2:16][CH2:17][CH2:18][CH3:19].[O-]CC.[Na+]>C(O)C>[CH2:16]([C:15]1[N:7]=[C:5]([C:4]2[CH:8]=[CH:9][CH:10]=[C:2]([F:1])[CH:3]=2)[NH:6][C:13](=[O:12])[CH:14]=1)[CH2:17][CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 546075Methyl 3-oxoheptanoateHCID 2723922Sodium ethoxideHCID 36393453-fluorobenzenecarboximidamide

Product 1

HCID 135788278HCID 135788278, compoundYield 57.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 3-fluorobenzamidine (1.14 g) and 3-oxoheptanoic acid methyl ester (1.0 g, Fluka, USA) in 15 mL of ethanol was added 3.15 mL of a 3 M solution of sodium ethoxide in ethanol. The mixture was heated to reflux for 48 h, allowed to cool to room temperature, and the volatiles were removed in vacuo. The residue was dissolved in chloroform and washed with water three times. The aqueous extractions were combined, acidified to pH=6, and washed three times with ethyl acetate. All organic layers were combined, dried over magnesium sulfate, and concentrated in vacuo. The product was purified by column chromatography using 60% ethyl acetate in hexanes as the mobile phase to yield 6-butyl-2-(3-fluorophenyl)-3H-pyrimidin-4-one (0.9 g).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 48 h
  3. customthe volatiles were removed in vacuo
  4. dissolutionThe residue was dissolved in chloroform
  5. washwashed with water three times
  6. extractionThe aqueous extractions
  7. washwashed three times with ethyl acetate
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated in vacuo
  10. customThe product was purified by column chromatography

Sources & evidence

ORD record
ord-a64dd9d6588d48ada9d82f4169286814
Source dataset
uspto-grants-2006_05
Patent number
US07037916B2

Reaction notes

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