StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Ethanol → 2-(2-(2-Oxoimidazolidin-1-yl)ethylamino)-4-(5-(thiophen-2-yl)thiophen-2-yl)pyrimidine-5-carbonitrile

HRID 2267437
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2267437
Br[C:2]1[S:6][C:5]([C:7]2[C:12]([C:13]#[N:14])=[CH:11][N:10]=[C:9]([NH:15][CH2:16][CH2:17][N:18]3[CH2:22][CH2:21][NH:20][C:19]3=[O:23])[N:8]=2)=[CH:4][CH:3]=1.[S:24]1[CH:28]=[CH:27][CH:26]=[C:25]1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].C(O)C>ClCCl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[O:23]=[C:19]1[NH:20][CH2:21][CH2:22][N:18]1[CH2:17][CH2:16][NH:15][C:9]1[N:8]=[C:7]([C:5]2[S:6][C:2]([C:25]3[S:24][CH:28]=[CH:27][CH:26]=3)=[CH:3][CH:4]=2)[C:12]([C:13]#[N:14])=[CH:11][N:10]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 27339602-Thiopheneboronic acidHCID 602045694-(5-Bromothiophen-2-yl)-2-(2-(2-oxoimidazolidin-1-yl)ethylamino)pyrimidine-5-carbonitrile

Produkt 1

HCID 602045672-(2-(2-Oxoimidazolidin-1-yl)ethylamino)-4-(5-(thiophen-2-yl)thiophen-2-yl)pyrimidine-5-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

4-(5-Bromothiophen-2-yl)-2-(2-(2-oxoimidazolidin-1-yl)ethylamino)pyrimidine-5-carbonitrile (0.08 g, 0.2 mmol), thiophen-2-ylboronic acid (0.052 g, 04 mmol), sodium carbonate (1.5 mL of 2 M solution, 1 mmol) were added to a microwave tube containing ethanol (1.5 mL). The tube was flushed with nitrogen and tetrakis(triphenylphosphine)palladium (0.06 g, 0.054 mmol) was added. The tube was capped and heated to 130° C. for 30 min in a Personal Chemistry microwave. The reaction was diluted with dichloromethane and washed with saturated aqueous sodium bicarbonate, water and brine. The organic layer was then dried with sodium sulfate, reduced in vacuo and purified by flash chromatography on silica gel using a gradient of 0 to 10% methanol in dichloromethane to afford a yellow solid which recrystallized from ethyl acetate. Yield=0.066 g. MS (M+H)+ 397.

Aufarbeitung

  1. additionwas added
  2. customThe tube was capped
  3. washwashed with saturated aqueous sodium bicarbonate, water and brine
  4. dry with materialThe organic layer was then dried with sodium sulfate
  5. custompurified by flash chromatography on silica gel using a gradient of 0 to 10% methanol in dichloromethane
  6. customto afford a yellow solid which
  7. customrecrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-13821481fe2d4cca99d88871ec9c51f6
Quelldatensatz
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07858785B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion