Acetone → Sildenafil

HRID 1435819Notes

Reaction equation

HRID 1435819 reaction equation
[CH3:1][N:2]1[C:10]2[C:9](=[O:11])[N:8]=[C:7]([C:12]3[C:13](C4C=CC(OCC)=CC=4)=[C:14]([S:18](Cl)(=[O:20])=[O:19])[CH:15]=[CH:16][CH:17]=3)[NH:6][C:5]=2[C:4]([CH2:31][CH2:32][CH3:33])=[N:3]1.[OH-].[Na+].[CH3:36][N:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1.[CH3:43][C:44](C)=[O:45]>>[CH3:33][CH2:32][CH2:31][C:4]1[C:5]2[N:6]=[C:7]([C:12]3[CH:13]=[C:14]([S:18]([N:40]4[CH2:41][CH2:42][N:37]([CH3:36])[CH2:38][CH2:39]4)(=[O:19])=[O:20])[CH:15]=[CH:16][C:17]=3[O:45][CH2:44][CH3:43])[NH:8][C:9](=[O:11])[C:10]=2[N:2]([CH3:1])[N:3]=1

Participants

5

Reactant 4

HCID 180AcetoneHCID 14798Sodium HydroxideHCID 531671-MethylpiperazineHCID 178440326HCID 178440326, compound

Product 1

HCID 135398744SildenafilYield 88.8%

Conditions

Temperature
0 °C

Procedure

In a 3-necked flask, 3-(4,7-dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo(4,3-d)pyrimidin-5-yl)-(4-ethoxyphenyl)benzene sulfonyl chloride (5 g, 12.2 mmol) was mixed with acetone (100 ml) at room temperature, then aqueous NaOH 47% (0.487 g, 10 mmol) was added. N-methyl piperazine (1.34 g, 11 mmol) was added dropwise. The reaction mixture was stirred for 45 mm, then cooled to 0° C. and filtered. The precipitate was washed with water twice and dried at 50° C. under 10 mm Hg to give sildenafil in a 88.8% yield.

Workup

  1. filtrationfiltered
  2. washThe precipitate was washed with water twice
  3. customdried at 50° C. under 10 mm Hg

Sources & evidence

ORD record
ord-186838e704174a59bedc5a7414c9b3fc
Source dataset
uspto-grants-2009_11
Patent number
US07618976B2

Reaction notes

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