Potassium Hydroxide → HCID 178461171, compound

HRID 82345Notes

Reaction equation

HRID 82345 reaction equation
[CH3:1][C@@H:2]1[CH2:6][CH2:5][C:4](=O)[CH:3]1[C:8]([O:10]CC)=O.[NH2:13][C:14]([NH2:16])=[S:15].[OH-].[K+]>C(O)C.O>[SH:15][C:14]1[N:13]=[C:8]([OH:10])[C:3]2[C@H:2]([CH3:1])[CH2:6][CH2:5][C:4]=2[N:16]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 2723790ThioureaHCID 11052075Ethyl (2R)-2-methyl-5-oxocyclopentane-1-carboxylate

Product 1

HCID 178461171HCID 178461171, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of a mixture of (2R)-ethyl 2-methyl-5-oxocyclopentanecarboxylate (20 g, 117.5 mmol) and thiourea (9.2 g, 120.9 mmol) in ethanol (100 mL) was added KOH (8.3 g, 147.9 mmol) in water (60 mL). The mixture was refluxed for 10 hours. After cooling, the solvent was removed and the residue was neutralized with concentrated HCl (12 mL) at 0° C. and then extracted with DCM (3×150 mL). The solvent was removed and the residue was purified by silica gel chromatography, eluting with Hexane/ethyl acetate (2:1) to give (R)-2-mercapto-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-ol (12 g, 56%). MS (APCI+) [M+H]+183.

Workup

  1. temperatureThe mixture was refluxed for 10 hours
  2. temperatureAfter cooling
  3. customthe solvent was removed
  4. customwas neutralized with concentrated HCl (12 mL) at 0° C.
  5. extractionextracted with DCM (3×150 mL)
  6. customThe solvent was removed
  7. customthe residue was purified by silica gel chromatography
  8. washeluting with Hexane/ethyl acetate (2:1)

Sources & evidence

ORD record
ord-d758629974174011b9039a2a1fc93f76
Source dataset
uspto-grants-2014_09
Patent number
US08846681B2

Reaction notes

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