Cesium carbonate → tert-Butyl-6-(((1S,2S)-2-(5-(2-hydroxypropan-2-yl)pyridin-2-yl)cyclopropyl)methoxy)-2-methylpyrimidin-4-yl((5-methyl-1,3,4-thiadiazol-2-yl)methyl)carbamate

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Reaktionsgleichung

Cl[C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([O:9][CH2:10][C@H:11]2[CH2:13][C@@H:12]2[C:14]2[N:19]=[CH:18][C:17]([C:20]([OH:23])([CH3:22])[CH3:21])=[CH:16][CH:15]=2)[CH:3]=1.[CH3:24][C:25]1[S:29][C:28]([CH2:30][NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[N:27][N:26]=1.C([O-])([O-])=O.[Cs+].[Cs+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1.CCOC(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:34]([O:33][C:32](=[O:38])[N:31]([C:2]1[CH:3]=[C:4]([O:9][CH2:10][C@H:11]2[CH2:13][C@@H:12]2[C:14]2[CH:15]=[CH:16][C:17]([C:20]([OH:23])([CH3:22])[CH3:21])=[CH:18][N:19]=2)[N:5]=[C:6]([CH3:8])[N:7]=1)[CH2:30][C:28]1[S:29][C:25]([CH3:24])=[N:26][N:27]=1)([CH3:37])([CH3:36])[CH3:35]

Komponenten

Reaktionsbedingungen

Temperatur: 85 °C

Versuchsvorschrift

The mixture of 8-3 (60 mg, 0.18 mmol), 8-4 (50 mg, 0.22 mmol), Cs2CO3 (88 mg, 0.27 mmol), Pd(OAc)2 (8.1 mg, 0.036 mmol), BINAP (25 mg, 0.040 mmol) in toluene (2.0 mL) was heated at 85° C. for overnight. Then the reaction mixture was diluted with EtOAc (20 mL), filtered and concentrated in vacuo to give crude product (94 mg) which was used for next step without further purification. LRMS (ES) calculated M+H for C26H34N6O4S: 527.24. Found: 527.2.

Aufarbeitung

filtrationfiltered
concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-129b659238bb44ecbe90d2caf4204167
Quelldatensatz: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09062059B2

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