Potassium Hydroxide → HCID 178518551, compound

HRID 559411Notes

Reaction equation

HRID 559411 reaction equation
O=[C:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[C:7]([O:9]C)=O.[NH2:11][C:12]([NH2:14])=[S:13].[OH-].[K+]>C(O)C.O>[SH:13][C:12]1[N:11]=[C:7]([OH:9])[C:3]2[CH2:4][CH2:5][CH2:6][C:2]=2[N:14]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 66328Cyclopentanecarboxylic acid, 2-oxo-, methyl esterHCID 2723790Thiourea

Product 1

HCID 178518551HCID 178518551, compoundYield 26.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of the methyl 2-oxocyclopentanecarboxylate (40 g, 281 mmol) and thiourea (21 g, 281 mmol) in ethanol (200 ml) was added KOH (20 g, 356 mmol) in water (120 ml). The mixture was refluxed for 12 hour. The solvent was removed and the residue was quenched with concentrated HCl (25 mL). The precipitate was filtered, washed with water and dried to afford the 2-mercapto-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-ol (12.5 g, 26%). MS (APCI+) [M+H]+168.

Workup

  1. temperatureThe mixture was refluxed for 12 hour
  2. customThe solvent was removed
  3. customthe residue was quenched with concentrated HCl (25 mL)
  4. filtrationThe precipitate was filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-3d36450890d04e23936efaa0f1926944
Source dataset
uspto-grants-2011_11
Patent number
US08063050B2

Reaction notes

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