Acetonitrile → 2-Chloro-4-(5-methylthiophen-2-yl)pyrimidine

HRID 507580

Reaktionsgleichung

Reaktionsgleichung von HRID 507580
[CH3:1][C:2]1[S:6][C:5](B(O)O)=[CH:4][CH:3]=1.[Cl:10][C:11]1[N:16]=[C:15](Cl)[CH:14]=[CH:13][N:12]=1.C([O-])([O-])=O.[Na+].[Na+].CC#N>C(Cl)Cl.CO.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>[Cl:10][C:11]1[N:16]=[C:15]([C:5]2[S:6][C:2]([CH3:1])=[CH:3][CH:4]=2)[CH:14]=[CH:13][N:12]=1

Komponenten

8

Edukt 4

HCID 6342AcetonitrileHCID 10340Sodium CarbonateHCID 775312,4-DichloropyrimidineHCID 2734374(5-Methylthiophen-2-yl)boronic acid

Produkt 1

HCID 574288352-Chloro-4-(5-methylthiophen-2-yl)pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 0.20 g (1.4 mmol) of 5-methyl-2-thiopheneboronic acid, 0.21 g (1.4 mmol) of 2,4-dichloropyrimidine and 49 mg (0.070 mmol) of bis(triphenylphosphine)palladium(II) chloride in 2 mL of a 2 M Na2CO3 aqueous solution and 5 mL of MeCN was heated in a microwave for 10 min at 160° C., then cooled to rt, diluted with CH2Cl2 and MeOH, and dried over MgSO4. The organic solvent was removed in vacuo, and the resulting solid was purified by flash chromatography eluting with a linear gradient of 50% EtOAc in hexane to neat EtOAc to deliver the title compound. MS (M+H)+ 211.

Aufarbeitung

  1. dry with materialdried over MgSO4
  2. customThe organic solvent was removed in vacuo
  3. customthe resulting solid was purified by flash chromatography
  4. washeluting with a linear gradient of 50% EtOAc in hexane to neat EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-5b943c080c274e139a25b9d55fb6c580
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07786132B2

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