2-Methoxyaniline → 2-(3-Hydroxyphenyl)-9-(2-methoxyphenyl)-9H-purine-6-carboxamide

HRID 391620Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 391620
ClC1N=C(C(OCC)=O)C([N+]([O-])=O)=[C:4]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[O:23][CH3:24])N=1.Cl[C:26]1[N:31]=[C:30]([C:32]([O:34]CC)=O)[C:29]([N+:37]([O-])=O)=[C:28](Cl)[N:27]=1.C[O:42][C:43]1[CH:49]=[CH:48][CH:47]=[CH:46][C:44]=1N.C([N:53](C(C)C)CC)(C)C>O1CCCC1>[OH:42][C:43]1[CH:44]=[C:46]([C:26]2[N:27]=[C:28]3[C:29]([N:37]=[CH:4][N:16]3[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[O:23][CH3:24])=[C:30]([C:32]([NH2:53])=[O:34])[N:31]=2)[CH:47]=[CH:48][CH:49]=1

Komponenten

6

Edukt 4

HCID 70002-MethoxyanilineHCID 81531DiisopropylethylamineHCID 2761044Ethyl 2,6-dichloro-5-nitropyrimidine-4-carboxylateHCID 57474573Ethyl 2-chloro-6-(2-methoxyphenylamino)-5-nitropyrimidine-4-carboxylate

Produkt 1

HCID 574745682-(3-Hydroxyphenyl)-9-(2-methoxyphenyl)-9H-purine-6-carboxamideAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Ethyl 2-chloro-6-(2-methoxyphenylamino)-5-nitropyrimidine-4-carboxylate. In a 250 mL round-bottomed flask was placed ethyl 2,6-dichloro-5-nitropyrimidine-4-carboxylate (2 g, 7.52 mmol) in tetrahydrofuran (50 mL) and the mixture was cooled down to −78° C. A solution of 2-methoxyaniline (0.763 mL, 6.77 mmol) and diisopropylethyl amine (1.313 mL, 7.52 mmol) in 4 mL of tetrahydrofuran was added dropwise and the reaction was allowed to warm to room temperature overnight. Solvent was removed under reduced pressure and the crude material was purified by column chromatography (SiO2, 90% nHexanes in ethyl acetate) to provide the title compound as an orange solid (2.42 g, 6.86 mmol, 91% yield). MS (ESI) m/z 353.3 [M+1]+.

Aufarbeitung

  1. customIn a 250 mL round-bottomed flask was placed
  2. customSolvent was removed under reduced pressure
  3. customthe crude material was purified by column chromatography (SiO2, 90% nHexanes in ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-134e323cc05541a99db0158b9c620909
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08383634B2

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