Dimethylformamide → HCID 178489573, Verbindung

HRID 391645Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 391645
[OH:1][C@H:2]1CC[C@H](NC2N=C(C(OCC)=O)C([N+]([O-])=O)=C(NC3C=CC=CC=3OC)N=2)CC1.Cl[C:33]1[N:38]=[C:37]([C:39]([O:41]CC)=O)[C:36]([N+:44]([O-])=O)=[C:35]([NH:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][C:49]=2[O:54][CH3:55])[N:34]=1.[NH2:56][C@H:57]1[CH2:62][CH2:61][C@H:60]([OH:63])[CH2:59][CH2:58]1.C([N:67](C(C)C)CC)(C)C.C[N:74](C)[CH:75]=[O:76]>>[C:75](=[O:76])([O:63][C@H:60]1[CH2:61][CH2:62][C@H:57]([NH:56][C:33]2[N:34]=[C:35]3[C:36]([NH:44][C:2](=[O:1])[N:47]3[C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][C:49]=3[O:54][CH3:55])=[C:37]([C:39](=[O:41])[NH2:67])[N:38]=2)[CH2:58][CH2:59]1)[NH2:74]

Komponenten

6

Edukt 5

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 57474573Ethyl 2-chloro-6-(2-methoxyphenylamino)-5-nitropyrimidine-4-carboxylateHCID 178470296HCID 178470296, VerbindungHCID 178511715HCID 178511715, Verbindung

Produkt 1

HCID 178489573HCID 178489573, VerbindungAusbeute 82 %

Versuchsvorschrift

Ethyl 2-(trans-4-hydroxycyclohexylamino)-6-(2-methoxyphenylamino)-5-nitropyrimidine-4-carboxylate. Ethyl 2-chloro-6-(2-methoxyphenylamino)-5-nitropyrimidine-4-carboxylate (See Example 30.A) (0.300 g, 0.852 mmol), trans-4-aminocyclohexanol (0.117 g, 1.022 mmol) and diisopropylethylamine were reacted according to General Procedure C, except at room temperature and in dimethylformamide (5 ml). The crude reaction mixture was condensed and purified using Biotage chromatography (0-100% ethyl acetate in hexanes) to afford the title compound (0.303 g, 82%). MS (ESI) m/z 432.5 [M+1]+.

Aufarbeitung

  1. customThe crude reaction mixture
  2. customcondensed
  3. custompurified

Quellen und Nachweise

ORD-Eintrag
ord-ded6f95d08dc4a5ca0c250c902273e91
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08383634B2

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