Dimethyl Sulfide → 2-Chloro-4-(methylamino)-5-pyrimidinecarboxaldehyde

HRID 1988592Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1988592
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH3:9])[C:5]([CH:10]=C)=[CH:4][N:3]=1.[O:12]=[O+][O-].CSC>C(Cl)(Cl)Cl.CO>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH3:9])[C:5]([CH:10]=[O:12])=[CH:4][N:3]=1

Komponenten

5

Edukt 3

HCID 1068Dimethyl SulfideHCID 24823OzoneHCID 714147842-Chloro-5-ethenyl-N-methylpyrimidin-4-amine

Produkt 1

HCID 722075022-Chloro-4-(methylamino)-5-pyrimidinecarboxaldehydeAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21584188Chloroform methanolLösungsmittel

Versuchsvorschrift

A solution of (2-chloro-5-vinyl-pyrimidin-4-yl)-methylamine (2.50 g, 14.7 mmol) in CHCl3/MeOH (15 mL/15 mL) is bubbled by ozone for 30 minutes and then passed by a stream of argon for 3 minutes at −78° C. The reaction mixture is allowed to warm up to room temperature and treated with dimethyl sulfide (3.24 mL, 44.1 mmol). The reaction mixture is concentrated under reduced pressure to give colorless oil that is purified by flash column chromatography (SiO2, EtOAc/Hx=1/3) over silica gel to give 2-chloro-4-methylamino-pyrimidine-5-carbaldehyde (2.40 g, 95%) as a white solid.

Aufarbeitung

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. customto give colorless oil that
  3. customis purified by flash column chromatography (SiO2, EtOAc/Hx=1/3) over silica gel

Quellen und Nachweise

ORD-Eintrag
ord-423e9c97743244679c6cf840bae9b0ac
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07642255B2

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