Sulfuric Acid → HCID 178437832, compound

HRID 619187Notes

Reaction equation

HRID 619187 reaction equation
[CH:1]1([N:6]2[C:10]3=[N:11][C:12]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][CH:23]=[CH2:24])[C:17]=4O)=[N:13][C:14](=[O:15])[C:9]3=[C:8]([CH2:26][CH3:27])[NH:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.S(=O)(=O)(O)[OH:29]>C(O)(=O)C>[CH:1]1([N:6]2[C:10]3=[N:11][C:12]([C:16]4[CH:21]=[CH:20][C:19]5[O:29][CH:23]([CH3:24])[CH2:22][C:18]=5[CH:17]=4)=[N:13][C:14](=[O:15])[C:9]3=[C:8]([CH2:26][CH3:27])[NH:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 178438998HCID 178438998, compound

Product 1

HCID 178437832HCID 178437832, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a suspension of 1-cyclopentyl-3-ethyl-6-[2-hydroxy-3-(2-propenyl)phenyl]pyrazolo[3,4-d]pyrimidin-4-one (1.0 g) in acetic acid (15 ml) was added sulfuric acid (15 ml) while cooling in an ice bath. The reaction mixture was warmed to room temperature and stirred overnight. The reaction mixture was poured into ice/water, a precipitate formed which was collected by filtration and washed with water. The product was purified by recrystallization from ether, followed by column chromatography on silica gel eluting with 25% EtOAc/hexane to afford 0.5 g of 1-cyclopentyl-3-ethyl-6-[2-methyl-2,3-dihydrobenzo[b]furan-5-yl]pyrazolo[3,4-d]pyrimidin-4-one, m.p. 164-165° C.

Workup

  1. temperaturewhile cooling in an ice bath
  2. customa precipitate formed which
  3. filtrationwas collected by filtration
  4. washwashed with water
  5. customThe product was purified by recrystallization from ether

Sources & evidence

ORD record
ord-9fc0a8fd1662471eaf27b31449f6a77f
Source dataset
uspto-grants-1999_09
Patent number
US05958929

Reaction notes

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