Chloroacetone → HCID 136388376, compound

HRID 354185Notes

Reaction equation

HRID 354185 reaction equation
[CH2:1]([O:5][C:6]1[N:11]=[CH:10][C:9]([C:12](=[S:14])[NH2:13])=[CH:8][C:7]=1[C:15]1[NH:16][C:17](=[O:28])[C:18]2[C:19](=[C:21]([CH2:25][CH2:26][CH3:27])[N:22]([CH3:24])[N:23]=2)[N:20]=1)[CH:2]([CH3:4])[CH3:3].Cl[CH2:30][C:31](=O)[CH3:32]>C(O)C>[CH2:1]([O:5][C:6]1[C:7]([C:15]2[NH:16][C:17](=[O:28])[C:18]3[C:19](=[C:21]([CH2:25][CH2:26][CH3:27])[N:22]([CH3:24])[N:23]=3)[N:20]=2)=[CH:8][C:9]([C:12]2[S:14][CH:30]=[C:31]([CH3:32])[N:13]=2)=[CH:10][N:11]=1)[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 6571ChloroacetoneHCID 135730630HCID 135730630, compound

Product 1

HCID 136388376HCID 136388376, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6-Isobutoxy-5-(2-methyl-7-oxo-3-propyl-6,7-dihydro-2H-pyrazolo[4,3-d]-pyrimidin-5-yl)-3-pyridinecarbothioamide (Example 37) (77 mg, 0.19 mmol) and chloroacetone (36 mg, 0.38 mmol) were heated to reflux for 14 h in ethanol (5 mL). The reaction mixture was cooled and concentrated. Purification by flash column chromatography (gradient elution from 100% dichloromethane to 3% methanol:dichloromethane) gave 65 mg of product.

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated
  3. customPurification
  4. washby flash column chromatography (gradient elution from 100% dichloromethane to 3% methanol:dichloromethane)

Sources & evidence

ORD record
ord-333d42856266463bbd2dfcc9bc7a8c57
Source dataset
uspto-grants-2004_06
Patent number
US06756373B1

Reaction notes

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