Water → HCID 71534185, Verbindung

HRID 1410093

Reaktionsgleichung

Reaktionsgleichung von HRID 1410093
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[N:10]=[CH:9][S:8][C:6]=2[N:7]=1.[CH3:12][O:13][C:14]1[CH:15]=[C:16]([NH2:22])[CH:17]=[CH:18][C:19]=1[O:20][CH3:21].CCN(C(C)C)C(C)C.O>CS(C)=O>[Cl:1][C:2]1[N:3]=[C:4]([NH:22][C:16]2[CH:17]=[CH:18][C:19]([O:20][CH3:21])=[C:14]([O:13][CH3:12])[CH:15]=2)[C:5]2[N:10]=[CH:9][S:8][C:6]=2[N:7]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 227703,4-DimethoxyanilineHCID 81531DiisopropylethylamineHCID 6096395,7-Dichlorothiazolo(5,4-d)pyrimidine

Produkt 1

HCID 71534185HCID 71534185, VerbindungAusbeute 82,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

A mixture of 5,7-dichlorothiazolo[5,4-d]pyrimidine (0.925 g, 4.49 mmol), 3,4-dimethoxybenzenamine (0.89 g, 5.8 mmol) and DIEA (0.86 g, 6.66 mmol) in 12 mL of DMSO was stirred at room temperature for 24 hours. Then the reaction mixture was poured into 50 mL of water, the solid was filtered and washed with water (50 mL) to give a crude product as a solid. It was purified by silica gel chromatography (silica gel 200-300 mesh, eluting with ethyl acetate) to give 5-chloro-N-(3,4-dimethoxyphenyl)thiazolo[5,4-d]pyrimidin-7-amine (1.2 g, 82.8%) as a grey solid. LC-MS: 322.9 [M+H]+, tR=1.51 min.

Aufarbeitung

  1. filtrationthe solid was filtered
  2. washwashed with water (50 mL)
  3. customto give a crude product as a solid
  4. customIt was purified by silica gel chromatography (silica gel 200-300 mesh, eluting with ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-45b3fadfb00d4288b0af4ae254ea6cdf
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08921383B2

Verknüpfte Notizen

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