Diisopropylethylamine → (R)-9-(2-Methoxyphenyl)-8-oxo-2-(pyrrolidin-3-ylamino)-8,9-dihydro-7H-purine-6-carboxamide

HRID 391647Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 391647
C(OC([N:8]1[CH2:12][CH2:11][C@@H:10]([NH:13][C:14]2[N:19]=[C:18]([C:20](OCC)=[O:21])[C:17]([N+:25]([O-])=O)=[C:16]([NH:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[O:35][CH3:36])[N:15]=2)[CH2:9]1)=O)(C)(C)C.ClC1N=C([C:44](OCC)=[O:45])C([N+]([O-])=O)=C(NC2C=CC=CC=2OC)N=1.C([N:68]1CCC(N)C1)(OC(C)(C)C)=O.C(N(C(C)C)CC)(C)C>CN(C)C=O>[CH3:36][O:35][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=1[N:28]1[C:44](=[O:45])[NH:25][C:17]2[C:16]1=[N:15][C:14]([NH:13][C@@H:10]1[CH2:11][CH2:12][NH:8][CH2:9]1)=[N:19][C:18]=2[C:20]([NH2:68])=[O:21]

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 27563701-Boc-3-aminopyrrolidineHCID 57474573Ethyl 2-chloro-6-(2-methoxyphenylamino)-5-nitropyrimidine-4-carboxylateHCID 86627704(R)-Ethyl 2-(1-(tert-butoxycarbonyl)pyrrolidin-3-ylamino)-6-(2-methoxyphenylamino)-5-nitropyrimidine-4-carboxylate

Produkt 1

HCID 24937106(R)-9-(2-Methoxyphenyl)-8-oxo-2-(pyrrolidin-3-ylamino)-8,9-dihydro-7H-purine-6-carboxamideAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

(R)-Ethyl 2-(1-(tert-butoxycarbonyl)pyrrolidin-3-ylamino)-6-(2-methoxyphenylamino)-5-nitropyrimidine-4-carboxylate. Ethyl 2-chloro-6-(2-methoxyphenylamino)-5-nitro-pyrimidine-4-carboxylate (See Example 30.A) (0.300 g, 0.852 mmol), (R) 1-boc-3-aminopyrrolidine (0.190 g, 1.022 mmol) and diisopropylethylamine (0.164 g, 1.27 mmol) 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 (0.403 g, 94%). MS (ESI) m/z 503 [M+1]+.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-4df211e8443940cf8430fe2660fbe6f9
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08383634B2

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