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Cesium carbonate → tert-Butyl 4-(4-(tert-butoxycarbonylamino)naphthalen-1-yloxy)pyrimidin-2-ylcarbamate

HRID 2069150
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2069150
[C:1](=[O:8])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])[NH2:2].Cl[C:10]1[N:15]=[C:14]([O:16][C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:19][CH:18]=2)[CH:13]=[CH:12][N:11]=1.C([O-])([O-])=O.[Cs+].[Cs+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>C1COCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:30]([O:29][C:28]([NH:27][C:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:17]([O:16][C:14]2[CH:13]=[CH:12][N:11]=[C:10]([NH:2][C:1](=[O:8])[O:3][C:4]([CH3:7])([CH3:6])[CH3:5])[N:15]=2)=[CH:18][CH:19]=1)=[O:34])([CH3:33])([CH3:32])[CH3:31]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 77922tert-Butyl carbamateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 86660490tert-Butyl 4-(2-chloropyrimidin-4-yloxy)naphthalen-1-ylcarbamate

Produkt 1

HCID 68322851tert-Butyl 4-(4-(tert-butoxycarbonylamino)naphthalen-1-yloxy)pyrimidin-2-ylcarbamate
Ausbeute 56,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

To a degassed suspension of tert-butyl carbamate (1.89 g, 16.1 mmol), tert-butyl 4-(2-chloropyrimidin-4-yloxy)naphthalen-1-ylcarbamate (2.00 g, 5.38 mmol), Cs2CO3 (4.38 g, 13.45 mmol) and Xanthphos (0.249 g, 0.430 mmol) in THF (50 mL) was added Pd2dba3 (197 mg, 0.215 mmol) and the reaction mixture was heated at 75° C. for 16 hr. The reaction mixture was cooled to RT and was partitioned between EtOAc (40 mL) and water (40 mL). The aq layer was separated and extracted with EtOAc (40 mL) and the combined organic extracts were dried (MgSO4) and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, EtOAc in isohexane, 15-60%, gradient elution to afford the title compound as an off-white solid (1.365 g 53%.); Rt 2.53 min (Method 2); m/z 453 (M+H)+, (ES+)+

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to RT
  2. customwas partitioned between EtOAc (40 mL) and water (40 mL)
  3. customThe aq layer was separated
  4. extractionextracted with EtOAc (40 mL)
  5. dry with materialthe combined organic extracts were dried (MgSO4)
  6. customevaporated in vacuo
  7. customThe residue was purified by flash column chromatography (
  8. washSiO2, EtOAc in isohexane, 15-60%, gradient elution

Quellen und Nachweise

ORD-Eintrag
ord-77d3cc6dd3ad404a874a7ccda7500e74
Quelldatensatz
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08299074B2

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