Potassium bis(trimethylsilyl)amide → 3-Ethyl-5-[5-(4-ethylpiperazin-1-ylsulphonyl)-2-(pyridin-2-yl)methoxypyridin-3-yl]-2-methyl-2,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

HRID 990239Notes

Reaction equation

HRID 990239 reaction equation
[CH2:1]([O:3][C:4]1[C:9]([C:10]2[NH:11][C:12](=[O:22])[C:13]3[C:14](=[C:16]([CH2:20][CH3:21])[N:17]([CH3:19])[N:18]=3)[N:15]=2)=[CH:8][C:7]([S:23]([N:26]2[CH2:31][CH2:30][N:29]([CH2:32][CH3:33])[CH2:28][CH2:27]2)(=[O:25])=[O:24])=[CH:6][N:5]=1)[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[K+]>N1C=CC=CC=1CO>[CH2:20]([C:16]1[N:17]([CH3:19])[N:18]=[C:13]2[C:12](=[O:22])[NH:11][C:10]([C:9]3[C:4]([O:3][CH2:1][C:2]4[CH:7]=[CH:8][CH:9]=[CH:4][N:5]=4)=[N:5][CH:6]=[C:7]([S:23]([N:26]4[CH2:31][CH2:30][N:29]([CH2:32][CH3:33])[CH2:28][CH2:27]4)(=[O:25])=[O:24])[CH:8]=3)=[N:15][C:14]=12)[CH3:21]

Participants

4

Reactant 2

HCID 3251421Potassium bis(trimethylsilyl)amideHCID 1358163675-[2-Ethoxy-5-(4-ethylpiperazin-1-ylsulphonyl)pyridin-3-yl]-3-ethyl-2-methyl-2,6-dihydro-7h-pyrazolo[4,3-d]pyrimidin-7-one

Product 1

HCID 1358163543-Ethyl-5-[5-(4-ethylpiperazin-1-ylsulphonyl)-2-(pyridin-2-yl)methoxypyridin-3-yl]-2-methyl-2,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-oneYield 91%

Reagents, catalysts & solvents 1

HCID 11474PiconolSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of the title compound of Example 78 (100 mg, 0.2 mmol), potassium bis(trimethylsilyl)amide (210 mg, 1.1 mmol) in pyridine-2-methanol (1 ml) was heated to 110° C. for 18 hours. The cooled mixture was partitioned between ethyl acetate (10 ml) and water (10 ml), and the phases separated. The aqueous layer was extracted with ethyl acetate (2×5 ml) and dichloromethane (10 ml), the combined organic solutions dried (Na2SO4) and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel, using methanol:ethyl acetate (10:90) as eluant, and triturated with ether, to afford the title compound (49 mg, 43%) as a solid.

Workup

  1. customThe cooled mixture was partitioned between ethyl acetate (10 ml) and water (10 ml)
  2. customthe phases separated
  3. extractionThe aqueous layer was extracted with ethyl acetate (2×5 ml) and dichloromethane (10 ml)
  4. dry with materialthe combined organic solutions dried (Na2SO4)
  5. customevaporated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel
  7. customtriturated with ether

Sources & evidence

ORD record
ord-49514c42ddb142009cd17baab1f2f9ac
Source dataset
uspto-grants-2002_10
Patent number
US06458951B2

Reaction notes

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