Ethyl 2-oxocyclopentanecarboxylate → 2-(5-chlorothiophen-2-yl)-3H,4H,5H,6H,7H-cyclopenta[d]pyrimidin-4-one

HRID 1508695Notes

Reaction equation

HRID 1508695 reaction equation
Cl.[Cl:2][C:3]1[S:7][C:6]([C:8]([NH2:10])=[NH:9])=[CH:5][CH:4]=1.O=[C:12]1[CH2:16][CH2:15][CH2:14][CH:13]1[C:17](OCC)=[O:18].C[O-].[Na+]>C(O)C>[Cl:2][C:3]1[S:7][C:6]([C:8]2[NH:10][C:17](=[O:18])[C:13]3[CH2:14][CH2:15][CH2:16][C:12]=3[N:9]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 69136Ethyl 2-oxocyclopentanecarboxylateHCID 10942334Sodium MethoxideHCID 457919985-Chlorothiophene-2-carboximidamide hydrochloride

Product 1

HCID 1362098512-(5-chlorothiophen-2-yl)-3H,4H,5H,6H,7H-cyclopenta[d]pyrimidin-4-oneYield 71%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 50-mL round bottomed flask was charged with 5-chlorothiophene-2-carboxamidine HCl salt (400 mg, ˜2 mmol, 1 eq.), ethyl 2-oxocyclopentanecarboxylate (320 mg, 2 mmol, 1 eq.), and ethanol (10 ml). To the mixture was added sodium methoxide (25 w % in methanol, 540 mg, 2.5 mmol, 1.25 eq.). The resulting mixture was stirred under reflux for 20 hr. After cooling to room temperature, the mixture was evaporated under reduced pressure to dryness and the residue was treated with 1N HCl (6 ml). Solid was collected by filtration and washed water followed by ether. The product thus obtained was forwarded to the next step without any further purification (360 mg, 71% yield).

Workup

  1. temperatureunder reflux for 20 hr
  2. customthe mixture was evaporated under reduced pressure to dryness
  3. additionthe residue was treated with 1N HCl (6 ml)
  4. filtrationSolid was collected by filtration
  5. washwashed water
  6. customThe product thus obtained
  7. customwas forwarded to the next step without any further purification (360 mg, 71% yield)

Sources & evidence

ORD record
ord-9f489849629a449791f8714bfdb76bb3
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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