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

HRID 354190Notes

Reaction equation

HRID 354190 reaction equation
[F-].[K+].[CH2:3]([O:7][C:8]1[C:13]([C:14]2[NH:15][C:16](=[O:30])[C:17]3[C:18](=[C:20]([CH2:28][CH3:29])[N:21]([CH2:23][CH2:24][N:25]([CH3:27])[CH3:26])[N:22]=3)[N:19]=2)=[CH:12][C:11]([C:31]#[C:32][Si](C)(C)C)=[CH:10][N:9]=1)[CH2:4][CH2:5][CH3:6]>CN(C)C=O.O.[Cl-].[Na+].O>[CH2:3]([O:7][C:8]1[C:13]([C:14]2[NH:15][C:16](=[O:30])[C:17]3[C:18](=[C:20]([CH2:28][CH3:29])[N:21]([CH2:23][CH2:24][N:25]([CH3:26])[CH3:27])[N:22]=3)[N:19]=2)=[CH:12][C:11]([C:31]#[CH:32])=[CH:10][N:9]=1)[CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 2

HCID 522689Potassium FluorideHCID 1356742305-(2-Butoxy-5-trimethylsilylethynyl-3-pyridinyl)-2-[2-(dimethylamino)-ethyl]-3-ethyl-2,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

Product 1

HCID 1356742315-(2-Butoxy-5-ethynyl-3-pyridinyl)-2-[2-(dimethylamino)ethyl]-3-ethyl-2,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-oneYield 111.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Potassium fluoride (72.5 mg, 1.25 mmol) was added to a stirred solution of 5-(2-butoxy-5-trimethylsilylethynyl-3-pyridinyl)-2-[2-(dimethylamino)-ethyl]-3-ethyl-2,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one (Example 45) (300 mg, 0.625 mmol) in N,N-dimethylformamide (10 mL) and water (2 mL) at room temperature. After 2 h the reaction mixture was poured into brine and extracted with ethyl acetate (2×100 mL) The organics were dried (MgSO4) and concentrated to give the product (285 mg) as a pale brown oil.

Workup

  1. extractionextracted with ethyl acetate (2×100 mL) The
  2. dry with materialorganics were dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-0b02a7c1f5054bfb94e401ce0b3af181
Source dataset
uspto-grants-2004_06
Patent number
US06756373B1

Reaction notes

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