Water → HCID 178437840, compound

HRID 619143Notes

Reaction equation

HRID 619143 reaction equation
[CH:1]1([N:6]2[C:10]3=[N:11][C:12]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=4[O:22]C)=[N:13][C:14](=[O:15])[C:9]3=[C:8]([CH2:24][CH3:25])[NH:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].C(S)CC.O>CN(C=O)C.C(O)(=O)C>[CH:1]1([N:6]2[C:10]3=[N:11][C:12]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=4[OH:22])=[N:13][C:14](=[O:15])[C:9]3=[C:8]([CH2:24][CH3:25])[NH:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 962WaterHCID 7848Propyl mercaptanHCID 24758Sodium hydrideHCID 178437839HCID 178437839, compound

Product 1

HCID 178437840HCID 178437840, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-cyclopentyl-3-ethyl-6-(2-methoxyphenyl)-pyrazolo[3,4-d]pyrimidin-4-one (0.5 g, 1.5 mmol) in DMF (10 ml) was added NaH (0.15 g, 3.75 mmol, 60% NaH in mineral oil). The reaction mixture was stirred for 20 minutes, then propanethiol (0.228 g, 3.0 mmol) was added and the mixture was stirred at room temperature for 4 hours, then at 110° C. for 9 hours. The reaction mixture was stripped to dryness and then water (15 ml) followed by acetic acid (1 ml) were added. A precipitate formed which was collected by filtration, washed with water and recrystallized by DARCO® treatment from ethyl acetate to afford 0.28 g (58%) of 1-cyclopentyl-3-ethyl-6-(2-hydroxyphenyl)-pyrazolo[3,4-d]pyrimidin-4-one, m.p. 272-273° C., as white fibrous needles.

Workup

  1. stirringthe mixture was stirred at room temperature for 4 hours
  2. waitat 110° C. for 9 hours
  3. additionwere added
  4. customA precipitate formed which
  5. filtrationwas collected by filtration
  6. washwashed with water
  7. customrecrystallized by DARCO® treatment from ethyl acetate

Sources & evidence

ORD record
ord-56e184b626ec4e349e1b1d3bcf30782a
Source dataset
uspto-grants-1999_09
Patent number
US05958929

Reaction notes

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