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1-Methoxy-2-propanol → 5-[5-Acetyl-2-(2-methoxy-1-methylethoxy)-3-pyridinyl]-3-ethyl-2-(2-methoxyethyl)-2,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

HRID 354178
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 354178
[C:1]([C:4]1[CH:5]=[C:6]([C:15]2[NH:16][C:17](=[O:30])[C:18]3[C:19](=[C:21]([CH2:28][CH3:29])[N:22]([CH2:24][CH2:25][O:26][CH3:27])[N:23]=3)[N:20]=2)[C:7](OCCCC)=[N:8][CH:9]=1)(=[O:3])[CH3:2].C[Si](C)(C)[N-][Si](C)(C)C.[K+].[CH3:41][O:42][CH2:43][CH:44]([OH:46])[CH3:45]>>[C:1]([C:4]1[CH:5]=[C:6]([C:15]2[NH:16][C:17](=[O:30])[C:18]3[C:19](=[C:21]([CH2:28][CH3:29])[N:22]([CH2:24][CH2:25][O:26][CH3:27])[N:23]=3)[N:20]=2)[C:7]([O:46][CH:44]([CH3:45])[CH2:43][O:42][CH3:41])=[N:8][CH:9]=1)(=[O:3])[CH3:2]
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Komponenten

4

Edukt 3

HCID 79001-Methoxy-2-propanolHCID 3251421Potassium bis(trimethylsilyl)amideHCID 1354846345-(5-Acetyl-2-butoxy-3-pyridinyl)-3-ethyl-2-(2-methoxyethyl)-2,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

Produkt 1

HCID 1354559455-[5-Acetyl-2-(2-methoxy-1-methylethoxy)-3-pyridinyl]-3-ethyl-2-(2-methoxyethyl)-2,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-oneAusbeute 29 %

Versuchsvorschrift

5-(5-Acetyl-2-butoxy-3-pyridinyl)-3-ethyl-2-(2-methoxyethyl)-2,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one (Example 16) (150 mg, 0.36 mmol) was dissolved in 1-methoxypropan-2-ol (3 mL) and the solution heated at reflux for 5 minutes to degas the solution. After cooling potassium hexamethyldisilazide (360 mg, 1.80 mmol) was added and the solution reheated to reflux for 8 h. The cooled reaction mixture was evaporated to dryness and partitioned between ethyl acetate and water after 1N hydrochloric acid had been used to adjust the pH to 8. The organic phase was separated and washed with brine, dried (MgSO4) and evaporated. The crude product was purified by flash column chromatography (gradient elution from 100% dichloromethane 0.5% ammonia to 99% dichloromethane:1% methanol:0.5% ammonia) to give the title compound (45 mg, 29%).

Aufarbeitung

  1. temperaturethe solution heated
  2. temperatureat reflux for 5 minutes
  3. customto degas the solution
  4. additionwas added
  5. temperatureto reflux for 8 h
  6. customThe cooled reaction mixture
  7. customwas evaporated to dryness
  8. custompartitioned between ethyl acetate and water after 1N hydrochloric acid
  9. customThe organic phase was separated
  10. washwashed with brine
  11. dry with materialdried (MgSO4)
  12. customevaporated
  13. customThe crude product was purified by flash column chromatography (gradient elution from 100% dichloromethane 0.5% ammonia to 99% dichloromethane:1% methanol:0.5% ammonia)

Quellen und Nachweise

ORD-Eintrag
ord-91dbe6bd52114a4881daa2e9fac3862f
Quelldatensatz
uspto-grants-2004_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06756373B1

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