Ethyl Acetate → 5-[2-(3-Aminophenylamino)-5-methyl-pyrimidin-4-yl]-4-cyclohexyl-2-methylsulfanyl-thiophene-3-carbonitrile

HRID 478192

Reaktionsgleichung

Reaktionsgleichung von HRID 478192
[N+:1]([C:4]1[CH:5]=[C:6]([NH:10][C:11]2[N:16]=[C:15]([C:17]3[S:21][C:20]([S:22][CH3:23])=[C:19]([C:24]#[N:25])[C:18]=3[CH:26]3[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]3)[C:14]([CH3:32])=[CH:13][N:12]=2)[CH:7]=[CH:8][CH:9]=1)([O-])=O.CCOC(C)=O>[Pd].CO>[NH2:1][C:4]1[CH:5]=[C:6]([NH:10][C:11]2[N:16]=[C:15]([C:17]3[S:21][C:20]([S:22][CH3:23])=[C:19]([C:24]#[N:25])[C:18]=3[CH:26]3[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]3)[C:14]([CH3:32])=[CH:13][N:12]=2)[CH:7]=[CH:8][CH:9]=1

Komponenten

5

Edukt 2

HCID 8857Ethyl AcetateHCID 220190285-[2-(3-Nitrophenylamino)-5-methyl-pyrimidin-4-yl]-4-cyclohexyl-2-methylsulfanyl-thiophene-3-carbonitrile

Produkt 1

HCID 220190265-[2-(3-Aminophenylamino)-5-methyl-pyrimidin-4-yl]-4-cyclohexyl-2-methylsulfanyl-thiophene-3-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A suspension of 5-[2-(3-Nitrophenylamino)-5-methyl-pyrimidin-4-yl]-4-cyclohexyl-2-methylsulfanyl-thiophene-3-carbonitrile (0.187 g, 402 umol) and 10% palladium on carbon in methanol was stirred under a hydrogen atmosphere overnight resulting in complete conversion to product as determined by TLC (40% EtOAc:hexanes). The reaction was filtered through celite and concentrated in vacuo to afford the desired amine V-8 (0.186 g, 426 umol) in quantitative yield. 1NMR (CDCl3) δ1.0-1.1(m, 10H), 2.1 (s, 3H), 2.6 (s, 3H), 6.2 (d, 1H), 6.8 (d, 1H), 6.9-7.0 (m, 3H) , 8.2 (s, 1H).

Aufarbeitung

  1. customresulting in complete conversion to product
  2. filtrationThe reaction was filtered through celite and
  3. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e653ffa9b68f4ccb8f7fb2aaf004ef35
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06642227B2

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