Acrylonitrile → 5-(4-Methoxyphenyl)-6-phenyl-N-{3-[2-cyanoethoxy]propyl}furo[2,3-d]pyrimidine-4-amine

HRID 1926879Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1926879
[C:1](#[N:4])[CH:2]=[CH2:3].CC[O-].[Na+].[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[C:25]3[C:24]([NH:26][CH2:27][CH2:28][CH2:29][OH:30])=[N:23][CH:22]=[N:21][C:20]=3[O:19][C:18]=2[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:13][CH:12]=1>CS(C)=O>[CH3:9][O:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[C:25]3[C:24]([NH:26][CH2:27][CH2:28][CH2:29][O:30][CH2:3][CH2:2][C:1]#[N:4])=[N:23][CH:22]=[N:21][C:20]=3[O:19][C:18]=2[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:15][CH:16]=1

Komponenten

5

Edukt 3

HCID 7855AcrylonitrileHCID 2723922Sodium ethoxideHCID 580168233-{[5-(4-Methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}propan-1-ol

Produkt 1

HCID 580168795-(4-Methoxyphenyl)-6-phenyl-N-{3-[2-cyanoethoxy]propyl}furo[2,3-d]pyrimidine-4-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Add 47 mg (0.89 mmol) acrylonitrile and 57 mg (0.83 mmol) sodium ethylate to 300 mg (0.80 mmol) of the compound from Stage 1. Stir the mixture overnight at 80° C. After cooling, take up the mixture in DMSO and purify directly by RP-HPLC (column: Gromsil 250 mm×30 mm, 10 μm; acetonitrile/water gradient: 0-3 min 5% acetonitrile, 3-50 min 5%→98% acetonitrile, 50-55 min 98% acetonitrile). 160 mg (47% of theor.) of the title compound is obtained as a yellow oil.

Aufarbeitung

  1. temperatureAfter cooling
  2. custompurify directly by RP-HPLC (column: Gromsil 250 mm×30 mm, 10 μm; acetonitrile/water gradient: 0-3 min 5% acetonitrile, 3-50 min 5%→98% acetonitrile, 50-55 min 98% acetonitrile)

Quellen und Nachweise

ORD-Eintrag
ord-8ed139b7c6bc4bf797d30a72ed8a48b3
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08183246B2

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