Potassium Fluoride → 5-(2-Butoxy-5-ethynyl-3-pyridinyl)-3-ethyl-2-(2-methoxyethyl)-2,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

HRID 354176Notes

Reaction equation

HRID 354176 reaction equation
[F-].[K+].[CH2:3]([O:7][C:8]1[C:13]([C:14]2[NH:15][C:16](=[O:29])[C:17]3[C:18](=[C:20]([CH2:27][CH3:28])[N:21]([CH2:23][CH2:24][O:25][CH3:26])[N:22]=3)[N:19]=2)=[CH:12][C:11]([C:30]#[C:31][Si](C)(C)C)=[CH:10][N:9]=1)[CH2:4][CH2:5][CH3:6]>CN(C)C=O.C(OCC)(=O)C>[CH2:3]([O:7][C:8]1[C:13]([C:14]2[NH:15][C:16](=[O:29])[C:17]3[C:18](=[C:20]([CH2:27][CH3:28])[N:21]([CH2:23][CH2:24][O:25][CH3:26])[N:22]=3)[N:19]=2)=[CH:12][C:11]([C:30]#[CH:31])=[CH:10][N:9]=1)[CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 2

HCID 522689Potassium FluorideHCID 1357306155-(2-Butoxy-5-trimethylsilylethynyl-3-pyridinyl)-3-ethyl-2-(2-methoxy-ethyl)-2,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

Product 1

HCID 1357306465-(2-Butoxy-5-ethynyl-3-pyridinyl)-3-ethyl-2-(2-methoxyethyl)-2,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-oneYield 99.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Potassium fluoride (22 mg, 0.38 mmol) was added to a stirred solution of the title compound from Example 14 (90 mg, 0.19 mmol) in aqueous N,N-dimethylformamide (2 mL N,N-dimethylformamide/0.2 mL water) at 0° C. After 10 min the reaction was allowed to warm to room temperature and stirred for 2 h. The reaction mixture was diluted with ethyl acetate and washed with water, 1 N hydrochloric acid (3 times) and brine. The organic layer was dried (MgSO4) and concentrated to give the title compound as a white solid (75 mg).

Workup

  1. washwashed with water, 1 N hydrochloric acid (3 times) and brine
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-4c50c656ab2441349cc95ed541cd4658
Source dataset
uspto-grants-2004_06
Patent number
US06756373B1

Reaction notes

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