Acetone → HCID 71237332, compound

HRID 2280691Notes

Reaction equation

HRID 2280691 reaction equation
[OH:1][C@H:2]1[CH2:6][CH2:5][CH2:4][C@@H:3]1[NH:7][C:8]1[C:13]([C:14]([NH2:16])=[O:15])=[CH:12][N:11]=[C:10](SC)[N:9]=1.[S:19]([O-:24])(O[O-])(=O)=[O:20].[K+].[K+].[CH3:27]C(C)=O>O>[OH:1][C@H:2]1[CH2:6][CH2:5][CH2:4][C@@H:3]1[NH:7][C:8]1[C:13]([C:14]([NH2:16])=[O:15])=[CH:12][N:11]=[C:10]([S:19]([CH3:27])(=[O:24])=[O:20])[N:9]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 10313463Potassium peroxymonosulphateHCID 71237194HCID 71237194, compound

Product 1

HCID 71237332HCID 71237332, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 4-((1S,2S)-2-hydroxycyclopentylamino)-2-(methylthio)pyrimidine-5-carboxamide (800 mg, 2.98 mmol) in acetone (10 mL) was added a solution of potassium peroxymonosulfate (4.66 g, 7.45 mmol) in water (10 mL), and the resulting mixture was stirred at room temperature for 2 h. When the starting material was consumed, the reaction mixture was partitioned between ethyl acetate (20 mL) and water (15 mL). The aqueous layer was extracted with ethyl acetate (20 mL×3). The combined organic layers were washed with brine, dried over sodium sulfate and filtered. The filtrate was evaporated in vacuo to give 4-((1S,2S)-2-hydroxycyclopentylamino)-2-(methylsulfonyl)pyrimidine-5-carboxamide (700 mg, 2.3 mmol, yield 78%) as a solid. MS (ESI): m/z 301.2 [M+1]+.

Workup

  1. customWhen the starting material was consumed
  2. customthe reaction mixture was partitioned between ethyl acetate (20 mL) and water (15 mL)
  3. extractionThe aqueous layer was extracted with ethyl acetate (20 mL×3)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-01fe04d441774d648379ee239ad92814
Source dataset
uspto-grants-2015_09
Patent number
US09139534B2

Reaction notes

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