Acetic Acid → HCID 178437871, compound

HRID 1600808Notes

Reaction equation

HRID 1600808 reaction equation
[CH:1]1([N:6]2[C:10]3=[N:11][C:12]([CH2:16][C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([O:23]C)[CH:18]=4)=[N:13][C:14](=[O:15])[C:9]3=[C:8]([CH2:25][CH3:26])[NH:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].C(S)CC.C(O)(=O)C>CN(C=O)C>[CH:1]1([N:6]2[C:10]3=[N:11][C:12]([CH2:16][C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([OH:23])[CH:18]=4)=[N:13][C:14](=[O:15])[C:9]3=[C:8]([CH2:25][CH3:26])[NH:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7848Propyl mercaptanHCID 24758Sodium hydrideHCID 178437872HCID 178437872, compound

Product 1

HCID 178437871HCID 178437871, compoundYield 61.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of 1-cyclopentyl-3-ethyl-6-(3-methoxyphenyl methyl)pyrazolo[3,4-d]pyrimidin-4-one (4.49 g, 13 mmol) in DMF (123 mL) was added 97% NaH (1.26 g), followed 20 minutes later by propanethiol (2.96 g, 39 mmol). The reaction mixture was heated at 130° C. overnight, cooled to room temperature and then ice water, followed by acetic acid were added. A precipitate formed which was collected by filtration, recrystallized from ether and dried at 110° C. and 2 mm Hg to afford 2.72 g of 1-cyclopentyl-3-ethyl-6-(3-hydroxyphenylmethyl)pyrazolo[3,4-d]pyrimidin-4-one, m.p. 195-197° C.

Workup

  1. temperaturecooled to room temperature
  2. additionwere added
  3. customA precipitate formed which
  4. filtrationwas collected by filtration
  5. customrecrystallized from ether
  6. customdried at 110° C.

Sources & evidence

ORD record
ord-ea1c4de4459e47728674ada5c19eaff5
Source dataset
uspto-grants-1999_11
Patent number
US05977118

Reaction notes

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