HCID 849409, Verbindung → HCID 59643067, Verbindung

HRID 2251085Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2251085
C([O:3][C:4]([C:6]1[C:7]([NH:14][C:15]2[N:16]([CH3:21])[N:17]=[C:18]([CH3:20])[CH:19]=2)=[N:8][C:9]([S:12][CH3:13])=[N:10][CH:11]=1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:21][N:16]1[C:15]([NH:14][C:7]2[C:6]([CH2:4][OH:3])=[CH:11][N:10]=[C:9]([S:12][CH3:13])[N:8]=2)=[CH:19][C:18]([CH3:20])=[N:17]1

Komponenten

4

Edukt 2

HCID 849409HCID 849409, VerbindungHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 59643067HCID 59643067, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a cold (0° C.) solution of 4-(2,5-dimethyl-2H-pyrazol-3-ylamino)-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester, 16, (2.0 g, 6.5 mmol) in THF (30 mL) is added dropwise lithium aluminum hydride (10.4 mL of IM solution in THF, 10.4 mmol). The reaction is stirred at 0° C. for 5 minutes, then the ice bath is removed and the mixture allowed to stir for 45 minutes at room temperature. The reaction is re-cooled to 0° C., and H2O (0.4 mL) added dropwise to the mixture. After stirring 10 min at 0° C., NaOH solution (0.4 mL of 2N solution) is added dropwise. After stirring an additional 10 min at 0° C., H2O (1.2 mL) is added to the mixture, and the mixture stirred at room temperature for 15 minutes. The resulting mixture dried (MgSO4), filtered and concentrated in vacuo. The resulting residue is purified over silica (5% MeOH//chloroform) to afford 1.0 g of the desired product: 1H NMR (300 MHz, CDCl3) δ 8.22 (s, NH), 7.89 (s, 1H), 6.22 (s, 1H), 4.72 (s, 2H), 3.68 (s, 3H), 2.47 (s, 3H), 2.26 (s, 3H); ESI+ MS: m/z (rel intensity) 266.0 (100, M++H).

Aufarbeitung

  1. customthe ice bath is removed
  2. stirringto stir for 45 minutes at room temperature
  3. temperatureThe reaction is re-cooled to 0° C.
  4. additionH2O (0.4 mL) added dropwise to the mixture
  5. stirringAfter stirring 10 min at 0° C.
  6. additionNaOH solution (0.4 mL of 2N solution) is added dropwise
  7. stirringAfter stirring an additional 10 min at 0° C.
  8. additionH2O (1.2 mL) is added to the mixture
  9. stirringthe mixture stirred at room temperature for 15 minutes
  10. dry with materialThe resulting mixture dried (MgSO4)
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo
  13. customThe resulting residue is purified over silica (5% MeOH//chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-a1a28bac626147868b12d861f40b94d2
Quelldatensatz
uspto-grants-2008_01
Patentnummer
US07319102B1

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