4-Isopropyl-2-(tributylstannyl)thiazole → 4-Isopropyl-2-(6-(4-methoxybenzyloxy)-2-(4-(trifluoromethyl)thiazol-2-yl)pyrimidin-4-yl)thiazole

HRID 530759Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 530759
Cl[C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[N:5]=[C:4]([C:18]2[S:19][CH:20]=[C:21]([C:23]([F:26])([F:25])[F:24])[N:22]=2)[N:3]=1.[CH:27]([C:30]1[N:31]=[C:32]([Sn](CCCC)(CCCC)CCCC)[S:33][CH:34]=1)([CH3:29])[CH3:28].COC1C=C(C2SC=C(C(F)(F)F)N=2)N=C(C2SC=C(C)N=2)C=1>C(Cl)Cl>[CH:27]([C:30]1[N:31]=[C:32]([C:2]2[CH:7]=[C:6]([O:8][CH2:9][C:10]3[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=3)[N:5]=[C:4]([C:18]3[S:19][CH:20]=[C:21]([C:23]([F:26])([F:25])[F:24])[N:22]=3)[N:3]=2)[S:33][CH:34]=1)([CH3:29])[CH3:28]

Komponenten

5

Edukt 3

HCID 575787544-Isopropyl-2-(tributylstannyl)thiazoleHCID 582826474-Chloro-6-(4-methoxy-benzyloxy)-2-(4-trifluoromethyl-thiazol-2-yl)pyrimidineHCID 681599974-Methoxy-2-(4-methyl-thiazol-2-yl)-6-(4-trifluoromethyl-thiazol-2-yl)-pyridine

Produkt 1

HCID 681600184-Isopropyl-2-(6-(4-methoxybenzyloxy)-2-(4-(trifluoromethyl)thiazol-2-yl)pyrimidin-4-yl)thiazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Compound 25 was synthesized from compound 285 (1.87 mmol) and compound 219 (2.43 mmol) as described for compound 22 at a temperature of 110° C. DCM was added and the mixture was washed sequentially with saturated NH4Cl and brine. The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure. The crude was purified two times by silica gel chromatography (eluent: petroleum ether/EtOAc 5 to 10% and petroleum ether/DCM 20 to 60%) to give compound 25 as a colorless oil in 31% yield.

Aufarbeitung

  1. washthe mixture was washed sequentially with saturated NH4Cl and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude was purified two times by silica gel chromatography (eluent: petroleum ether/EtOAc 5 to 10% and petroleum ether/DCM 20 to 60%)

Quellen und Nachweise

ORD-Eintrag
ord-33b8a1b3d38348b7a0b68675be497279
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09353100B2

Notizen zur Reaktion

Wird geladen…