Aniline → 9-Phenyl-2-(3-pyridyl)purine-6-carboxamide

HRID 391617Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 391617
ClC1N=C(C(OC)=O)C([N+]([O-])=O)=[C:4]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)N=1.Cl[C:23]1[N:28]=[C:27]([C:29]([O:31]C)=O)[C:26]([N+:33]([O-])=O)=[C:25](Cl)[N:24]=1.[NH2:37][C:38]1C=[CH:42][CH:41]=[CH:40][CH:39]=1.C([N:47](C(C)C)CC)(C)C>C1COCC1>[C:16]1([N:15]2[CH:4]=[N:33][C:26]3[C:25]2=[N:24][C:23]([C:41]2[CH:42]=[N:37][CH:38]=[CH:39][CH:40]=2)=[N:28][C:27]=3[C:29]([NH2:47])=[O:31])[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Komponenten

6

Edukt 4

HCID 6115AnilineHCID 81531DiisopropylethylamineHCID 10586879Methyl 2,6-dichloro-5-nitropyrimidine-4-carboxylateHCID 57474557Methyl 2-chloro-5-nitro-6-(phenylamino)pyrimidine-4-carboxylate

Produkt 1

HCID 249378619-Phenyl-2-(3-pyridyl)purine-6-carboxamideAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Methyl 2-chloro-5-nitro-6-(phenylamino)pyrimidine-4-carboxylate. A solution of Methyl 2,6-dichloro-5-nitropyrimidine-4-carboxylate (0.72 g, 2.87 mmol) in anhydrous THF (14 mL) was chilled to −78° C. under nitrogen. A solution of aniline (0.288 mL, 3.16 mmol) and diisopropylethylamine (1.50 mL, 8.61 mmol) in anhydrous THF (10 mL) was then added drop wise with stirring over 10 minutes. The reaction was stirred at −78° C. for 1 hour and then allowed to warm to room temperature. After 90 minutes, the solvent was evaporated and the resulting residue purified using chromatography on a normal phase silica gel column (0-10% ethyl acetate in hexanes). Fractions containing product were combined and the solvent evaporated to provide the title compound (0.545 g, 1.76 mmol, 61% yield). MS (ESI) m/z 309.4 [M+1]+.

Aufarbeitung

  1. stirringThe reaction was stirred at −78° C. for 1 hour
  2. waitAfter 90 minutes
  3. customthe solvent was evaporated
  4. customthe resulting residue purified
  5. additionFractions containing product
  6. customthe solvent evaporated

Quellen und Nachweise

ORD-Eintrag
ord-c1b72cf54f424cadb3e4e0e3802d52a2
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08383634B2

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