Iodoethane → Methyl {4,6-diamino-2-[6-fluoro-3-(2-fluorobenzyl)-1H-pyrazolo[4,3-b]pyridin-1-yl]pyrimidin-5-yl}ethylcarbamate

HRID 626619Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 626619
[NH2:1][C:2]1[C:7](NC(=O)OC)=[C:6]([NH2:13])[N:5]=[C:4]([N:14]2[C:22]3[C:17](=[N:18][CH:19]=[C:20]([F:23])[CH:21]=3)[C:16]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[F:31])=[N:15]2)[N:3]=1.C[Si]([N-:36][Si](C)(C)C)(C)C.[Na+].I[CH2:43][CH3:44].[C:45]([O:48][CH2:49]C)(=[O:47])C>C1COCC1>[NH2:13][C:6]1[C:7]([CH2:44][CH2:43][NH:36][C:45](=[O:47])[O:48][CH3:49])=[C:2]([NH2:1])[N:3]=[C:4]([N:14]2[C:22]3[C:17](=[N:18][CH:19]=[C:20]([F:23])[CH:21]=3)[C:16]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[F:31])=[N:15]2)[N:5]=1

Komponenten

6

Edukt 4

HCID 6340IodoethaneHCID 8857Ethyl AcetateHCID 2724254Sodium bis(trimethylsilyl)amideHCID 56963347Methyl {4,6-diamino-2-[6-fluoro-3-(2-fluorobenzyl)-1H-pyrazolo [4,3-b]pyridin-1-yl]pyrimidin-5-yl}carbamate

Produkt 1

HCID 86698876Methyl {4,6-diamino-2-[6-fluoro-3-(2-fluorobenzyl)-1H-pyrazolo[4,3-b]pyridin-1-yl]pyrimidin-5-yl}ethylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Under argon, 142 mg (0.33 mmol) of the compound from example 1 were initially charged in THF (9.5 ml), the mixture was cooled to 0° C. and 0.33 ml (0.33 mmol) of sodium bis(trimethylsilyl)amide (1.0 M in THF) was then added dropwise. The mixture was stirred at 0° C. for 30 min, and 35 μl (0.43 mmol) of iodoethane were then added dropwise. The reaction mixture was stirred at RT overnight. The reaction mixture was diluted with ethyl acetate and washed twice with saturated aqueous sodium bicarbonate solution. The organic phase was dried over magnesium sulfate, filtered and concentrated. The residue was chromatographed on silica gel (mobile phase dichloromethane:methanol 60:1) and the product fractions were concentrated. This gave 89 mg (59% of theory) of the title compound as a solid.

Aufarbeitung

  1. stirringThe reaction mixture was stirred at RT overnight
  2. washwashed twice with saturated aqueous sodium bicarbonate solution
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel (mobile phase dichloromethane:methanol 60:1)
  7. concentrationthe product fractions were concentrated

Quellen und Nachweise

ORD-Eintrag
ord-ee831e6ded404dda843f810e2978b050
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309239B2

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