Cesium carbonate → tert-butyl 4-[6-(1,3-benzodioxol-5-yl)-1-[(3-ethyl-1,2,4-oxadiazol-5-yl)methyl]-2,4-dioxo-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl]piperidine-1-carboxylate

HRID 1476628Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1476628
Br[C:2]1[S:10][C:9]2[C:8](=[O:11])[N:7]([CH:12]3[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]3)[C:6](=[O:25])[N:5]([CH2:26][C:27]3[O:31][N:30]=[C:29]([CH2:32][CH3:33])[N:28]=3)[C:4]=2[CH:3]=1.[O:34]1[C:38]2[CH:39]=[CH:40][C:41](B(O)O)=[CH:42][C:37]=2[O:36][CH2:35]1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.Cl[Pd]Cl>[O:34]1[C:38]2[CH:39]=[CH:40][C:41]([C:2]3[S:10][C:9]4[C:8](=[O:11])[N:7]([CH:12]5[CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:22])[CH3:23])=[O:19])[CH2:16][CH2:17]5)[C:6](=[O:25])[N:5]([CH2:26][C:27]5[O:31][N:30]=[C:29]([CH2:32][CH3:33])[N:28]=5)[C:4]=4[CH:3]=3)=[CH:42][C:37]=2[O:36][CH2:35]1

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 2734371(2H-1,3-benzodioxol-5-yl)boronic acidHCID 67258967Tert-butyl 4-{6-bromo-1-[(3-ethyl-1,2,4-oxadiazol-5-yl)methyl]-2,4-dioxo-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl}piperidine-1-carboxylate

Produkt 1

HCID 67258594tert-butyl 4-[6-(1,3-benzodioxol-5-yl)-1-[(3-ethyl-1,2,4-oxadiazol-5-yl)methyl]-2,4-dioxo-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl]piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11050900Dichlorobis(tricyclohexylphosphine)pallium (II)KatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Tert-butyl 4-{6-bromo-1-[(3-ethyl-1,2,4-oxadiazol-5-yl)methyl]-2,4-dioxo-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl}piperidine-1-carboxylate 405 mg, compound B99), 1,3-benzodioxol-5-ylboronic acid (368 mg), dichlorobis(tricyclohexylphosphine)palladium (137 mg) and aqueous cesium carbonate solution (1.39 ml, 2.0 M) in dioxane (18 ml) are reacted according to the procedure described in example B55 to afford the title compound after purification by flash column chromatography [silica gel, elution gradient: cyclohexane/EtOAc, 80/20 to 50/50 (v/v)] as a solid.

Quellen und Nachweise

ORD-Eintrag
ord-089b51ce96244c02accf7011999c5a56
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09018175B2

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