Dichloromethane → HCID 86686239, Verbindung

HRID 1021290Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1021290
[Si:1]([O:8][CH2:9][C:10]1[C:11]([F:28])=[C:12]([C:16]2[CH:17]=[N:18][C:19]([N:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)=[N:20][CH:21]=2)[CH:13]=[CH:14][CH:15]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].ClCCl.CCN(C(C)C)C(C)C.Cl[CH2:42][CH2:43][S:44](Cl)(=[O:46])=[O:45]>O.C(Cl)(Cl)Cl>[Si:1]([O:8][CH2:9][C:10]1[C:11]([F:28])=[C:12]([C:16]2[CH:17]=[N:18][C:19]([N:22]3[CH2:23][CH2:24][N:25]([S:44]([CH:43]=[CH2:42])(=[O:46])=[O:45])[CH2:26][CH2:27]3)=[N:20][CH:21]=2)[CH:13]=[CH:14][CH:15]=1)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3]

Komponenten

7

Edukt 4

HCID 6344DichloromethaneHCID 15385Ethanesulfonylchloride, 2-chloro-HCID 81531DiisopropylethylamineHCID 86686241HCID 86686241, Verbindung

Produkt 1

HCID 86686239HCID 86686239, VerbindungAusbeute 58,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

5-[3-({[tert-Butyl(dimethyl)silyl]oxy}methyl)-2-fluorophenyl]-2-(piperazin-1-yl)pyrim idine (500 mg) was mixed with dichloromethane (10 ml), and DIPEA (482 mg) and 2-chloroethanesulfonyl chloride (304 mg) were added thereto at 0° C., followed by stirring at 0° C. for 1.5 hours. CHCl3 and water were added to the reaction mixture, and the organic layer was washed with water and saturated brine, dried over Na2SO4, and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (EtOAc/hexane) to obtain 5-[3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-fluorophenyl]-2-[4-(vinylsulfonyl)piperazin-1-yl]pyrimidine (360 mg).

Aufarbeitung

  1. additionwere added
  2. customat 0° C.
  3. washthe organic layer was washed with water and saturated brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-805076aabb144df189acb0260a31b10c
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08716470B2

Notizen zur Reaktion

Wird geladen…