Potassium Hydroxide → HCID 178518551, compound

HRID 532747Notes

Reaction equation

HRID 532747 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-76461df989fd44adb82b23b657c90750
Source dataset
uspto-grants-2014_10
Patent number
US08853199B2

Reaction notes

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