Butanoic acid, 2-ethyl-3-oxo-, ethyl ester → 2-(5-chloro-2-thienyl)-5-ethyl-4-methyl-1H-pyrimidin-6-one

HRID 1508718Notes

Reaction equation

HRID 1508718 reaction equation
Cl.[Cl:2][C:3]1[S:7][C:6]([C:8]([NH2:10])=[NH:9])=[CH:5][CH:4]=1.[CH2:11]([CH:13]([C:19](=O)[CH3:20])[C:14](OCC)=[O:15])[CH3:12].C[O-].[Na+]>C(O)C>[Cl:2][C:3]1[S:7][C:6]([C:8]2[NH:10][C:14](=[O:15])[C:13]([CH2:19][CH3:20])=[C:11]([CH3:12])[N:9]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 79065Butanoic acid, 2-ethyl-3-oxo-, ethyl esterHCID 10942334Sodium MethoxideHCID 457919985-Chlorothiophene-2-carboximidamide hydrochloride

Product 1

HCID 1359966122-(5-chloro-2-thienyl)-5-ethyl-4-methyl-1H-pyrimidin-6-oneYield 51%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 250-mL round bottomed flask was charged with 5-chlorothiophene-2-carboxamidine HCl salt (6.81 g, 34.6 mmol, 1 eq.), ethyl 2-ethyl-3-oxo-butanoate (12 g, 72 mmol, 2 eq.), and ethanol (100 ml). To the mixture was added sodium methoxide (25 w % in methanol, 23 g, 107 mmol, 3 eq.). The resulting mixture was stirred under reflux for 7 hr. After cooling to room temperature, the mixture was evaporated under reduced pressure to dryness and the residue was treated with 2N HCl (60 ml). Solid was collected by filtration and washed with water followed by ether. The product thus obtained was forwarded to the next step without any further purification (4.53 g, 51% yield).

Workup

  1. temperatureunder reflux for 7 hr
  2. customthe mixture was evaporated under reduced pressure to dryness
  3. additionthe residue was treated with 2N HCl (60 ml)
  4. filtrationSolid was collected by filtration
  5. washwashed with water
  6. customThe product thus obtained
  7. customwas forwarded to the next step without any further purification (4.53 g, 51% yield)

Sources & evidence

ORD record
ord-dc1184c975df4159bd076eb2edcbfd7a
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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