1,2-Dichloroethane → 2-[N,N-bis(tert-butoxycarbonyl)amino]-5-(ter-butyl-dimethyl-silanyloxymethyl)-pyrimidin

HRID 1789865Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1789865
[C:1]([O:5][C:6]([N:8]([C:16]1[N:21]=[CH:20][C:19](Br)=[CH:18][N:17]=1)[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:23]([Si:27](C)(C)OC[Sn](CCCC)(CCCC)CCCC)([CH3:26])([CH3:25])[CH3:24].C([O:47][CH2:48][CH3:49])C.[F-].[K+].Cl[CH2:53]CCl>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:1]([O:5][C:6]([N:8]([C:16]1[N:21]=[CH:20][C:19]([C:48]([CH3:49])([CH3:53])[O:47][SiH2:27][C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:18][N:17]=1)[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

7

Edukt 5

HCID 111,2-DichloroethaneHCID 3283Diethyl EtherHCID 522689Potassium FluorideHCID 11977091tert-butyl N-(5-bromopyrimidin-2-yl)-N-((tert-butoxy)carbonyl)carbamateHCID 14270862Tert-butyl-dimethyl-(tributylstannylmethoxy)silane

Produkt 1

HCID 1317258312-[N,N-bis(tert-butoxycarbonyl)amino]-5-(ter-butyl-dimethyl-silanyloxymethyl)-pyrimidinAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 178418476HCID 178418476, VerbindungKatalysator2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 2-[N,N-bis(tert-butoxycarbonyl)amino]-5-bromopyrimidin (16.0 g, 45.0 mmol), tert-butyl-dimethyl-tributylstannanylmethoxy-silane (20.5 g, 47.1 mmol), and bis(triphenylphosphine)palladium(II) dichloride (1.00 g, 1.40 mmol) in 1,2-dichloroethane (50 mL) was stirred at reflux overnight. Additional bis(triphenylphosphine)palladium(II) dichloride (1.00 g, 1.40 mmol) was added and the solution was refluxed for 8 h. The mixture was cooled to 0° C. and diethyl ether (200 mL) was added followed by saturated aqueous potassium fluoride (50 mL). The mixture was stirred vigourously for 60 min and filtered. The organic phase was washed with water, dried and concentrated under reduced pressure. Flash chromatography (MeOH/CH2Cl2, 1:99) gave 2-[N,N-bis(tert-butoxycarbonyl)amino]-5-(tert-butyl-dimethyl-silanyloxymethyl)-pyrimidin (10.2 g, 55%).

Aufarbeitung

  1. temperatureat reflux overnight
  2. temperaturethe solution was refluxed for 8 h
  3. filtrationfiltered
  4. washThe organic phase was washed with water
  5. customdried
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-867b195600854178ac824c7615cb1d97
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07071175B1

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