(Diethylamino)sulfur trifluoride → 4-Chloro-6-(2-fluoropropan-2-yl)pyrimidine

HRID 2401199Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2401199
CCN(S(F)(F)[F:7])CC.[Cl:10][C:11]1[N:16]=[CH:15][N:14]=[C:13]([C:17](O)([CH3:19])[CH3:18])[CH:12]=1>C(Cl)Cl>[Cl:10][C:11]1[CH:12]=[C:13]([C:17]([F:7])([CH3:19])[CH3:18])[N:14]=[CH:15][N:16]=1

Komponenten

4

Edukt 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 867625832-(6-Chloropyrimidin-4-yl)propan-2-ol2×

Produkt 1

HCID 867625844-Chloro-6-(2-fluoropropan-2-yl)pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a stirred solution of DAST (0.153 mL, 1.159 mmol) in DCM (5 mL) was added 2-(6-chloro-4-pyrimidinyl)-2-propanol (Intermediate 28, 100 mg, 0.579 mmol) dissolved in DCM (5 mL) dropwise, and the resulting mixture stirred under argon at −78° C. for 4 hrs. The reaction mixture was quenched with excess saturated sodium bicarbonate solution (50 mL) and extracted with DCM (2×20 mL). The organic layers were collected and solvent was removed gently in vacuo. Crude product in DCM was taken into the next reaction without further purification.

Aufarbeitung

  1. customThe reaction mixture was quenched with excess saturated sodium bicarbonate solution (50 mL)
  2. extractionextracted with DCM (2×20 mL)
  3. customThe organic layers were collected
  4. customsolvent was removed gently in vacuo
  5. customCrude product in DCM was taken into the next reaction without further purification

Quellen und Nachweise

ORD-Eintrag
ord-3660b335b34844d592d26b9bae16f38b
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08796283B2

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