Sodium Chloride → (2S)-1-(4-(3-iodo-1-isopropyl-1H-pyrazol-4-yl)pyrimidin-2-ylamino)propan-2-ol

HRID 500713Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 500713
[I:1][C:2]1[C:6]([C:7]2[CH:12]=[CH:11][N:10]=[C:9](S(C)(=O)=O)[N:8]=2)=[CH:5][N:4]([CH:17]([CH3:19])[CH3:18])[N:3]=1.[NH2:20][CH2:21][C@@H:22]([OH:24])[CH3:23].CCCCCC.[Na+].[Cl-]>C1COCC1.CCOC(C)=O>[I:1][C:2]1[C:6]([C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH:20][CH2:21][C@@H:22]([OH:24])[CH3:23])[N:8]=2)=[CH:5][N:4]([CH:17]([CH3:19])[CH3:18])[N:3]=1

Komponenten

7

Edukt 4

HCID 5234Sodium ChlorideHCID 8058HexaneHCID 7311736(S)-(+)-1-Aminopropan-2-olHCID 578563434-(3-iodo-1-isopropyl-1H-pyrazol-4-yl)-2-(methylsulfonyl)pyrimidine

Produkt 1

HCID 57856239(2S)-1-(4-(3-iodo-1-isopropyl-1H-pyrazol-4-yl)pyrimidin-2-ylamino)propan-2-olAusbeute 96,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

A mixture of 4-(3-iodo-1-isopropyl-1H-pyrazol-4-yl)-2-(methylsulfonyl)pyrimidine B-1-2 (16 g, 40 mmol) and (s)-1-amino-propan-2-ol (9 g, 122 mmol) in THF (160 mL) was heated to reflux overnight. TLC (hexane: EtOAc=2:1) showed the reaction was complete, EtOAc (80 mL) and saturated aqueous NaCl (80 mL) were added to the mixture, and the layers were separated. The organic layer was separated, washed with saturated aqueous NaCl (30 mL), dried over Na2SO4 and concentrated to give (2S)-1-(4-(3-iodo-1-isopropyl-1H-pyrazol-4-yl)pyrimidin-2-ylamino)propan-2-ol (B-1-3) (15 g, 96.9%) as a brown oil.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. customthe layers were separated
  4. customThe organic layer was separated
  5. washwashed with saturated aqueous NaCl (30 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-1d4dff21e95d43808fb2a1eabfc04537
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772246B2

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