Water → HCID 178437856, compound

HRID 1597873Notes

Reaction equation

HRID 1597873 reaction equation
Cl.[CH:2]1([N:7]2[C:11]3=[N:12][C:13]([C:17]4[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=4)=[N:14][C:15](=[O:16])[C:10]3=[C:9]([CH2:24][CH3:25])[NH:8]2)[CH2:6][CH2:5][CH2:4][CH2:3]1.[CH3:26][S:27](Cl)(=[O:29])=[O:28].O>N1C=CC=CC=1>[CH4:2].[CH:2]1([N:7]2[C:11]3=[N:12][C:13]([C:17]4[CH:18]=[CH:19][C:20]([NH:23][S:27]([CH3:26])(=[O:29])=[O:28])=[CH:21][CH:22]=4)=[N:14][C:15](=[O:16])[C:10]3=[C:9]([CH2:24][CH3:25])[NH:8]2)[CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 178437851HCID 178437851, compound

Product 2

HCID 297MethaneHCID 178437856HCID 178437856, compoundYield 143.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of 1-cyclopentyl-3-ethyl-6-(4-aminophenyl)pyrazolo[3,4-d]pyrimidin-4-one hydrochloride 1/3 hydrate (0.61 g, 1.7 mmol) in dry pyridine (20 ml) in an ice bath was added methanesulfonyl chloride (0.49 g, 4.25 mmol). The reaction mixture was stirred at room temperature for about two days, the solvent was stripped to dryness and the residue was treated with water. The product was collected by filtration and recrystallized from ethanol, after DARCO® treatment, to afford 0.49 g (72%) of 1-cyclopentyl-3-ethyl-6-[4-(methylsulfonylamino)phenyl]pyrazolo[3,4-d]pyrimidin-4-one, m.p. 325° C. (dec.).

Workup

  1. filtrationThe product was collected by filtration
  2. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-dda4f38f03154d83b70aeaf2b04142f5
Source dataset
uspto-grants-1998_04
Patent number
US05736548

Reaction notes

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