Formamidine acetate → HCID 136364255, compound

HRID 1250991Notes

Reaction equation

HRID 1250991 reaction equation
CO.C[O-].[Na+].C(O)(=O)C.[CH:10]([NH2:12])=[NH:11].[F:13][CH:14]([CH2:23][CH2:24][CH2:25][CH3:26])[C:15](=O)[CH2:16][C:17](OCC)=[O:18]>CO>[F:13][CH:14]([C:15]1[N:12]=[CH:10][NH:11][C:17](=[O:18])[CH:16]=1)[CH2:23][CH2:24][CH2:25][CH3:26]

Participants

5

Reactant 3

HCID 160693Formamidine acetateHCID 15457007HCID 15457007, compoundHCID 23694274Sodium methanolate methanol

Product 1

HCID 136364255HCID 136364255, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution in which 3.80 g of ethyl 4-fluoro-3-oxooctanoate had been dissolved in 10 ml of methanol were added 8.97 g of a 28% sodium methoxide methanol solution and 3.72 g of formamidine acetate, and the mixture was stirred at 60° C. for 5 hours. Then, the reaction mixture was concentrated under reduced pressure. To the concentrated solution were added 30 ml of water and 5.0 g of conc. hydrochloric acid, followed by cooling the mixture to 10 C, and the precipitated crystals were separated by filtration. These crystals were recrystallized from 20 ml of 2-propanol to obtain 2.30 g of 6-(1-fluoropentyl)-4-pyrimidone (isolated yield: 67.1%).

Workup

  1. concentrationThen, the reaction mixture was concentrated under reduced pressure
  2. additionTo the concentrated solution were added 30 ml of water and 5.0 g of conc. hydrochloric acid
  3. temperatureby cooling the mixture to 10 C
  4. customthe precipitated crystals were separated by filtration
  5. customThese crystals were recrystallized from 20 ml of 2-propanol

Sources & evidence

ORD record
ord-286e781ded9a4fd48556b98a32ff70f7
Source dataset
uspto-grants-2002_01
Patent number
US06340757B1

Reaction notes

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