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Dimethylformamide dimethyl acetal → 5-[2-(3-Nitrophenylamino)-5-methyl-pyrimidin-4-yl]-4-cyclohexyl-2-methylsulfanyl-thiophene-3-carbonitrile

HRID 478191
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 478191
[CH:1]1([C:7]2[C:8]([C:22]#[N:23])=[C:9]([S:20][CH3:21])[S:10][C:11]=2[C:12](=O)[C:13]([CH3:18])=[CH:14]N(C)C)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CN(C(OC)OC)C.[N+:32]([C:35]1[CH:36]=[C:37]([NH:41][C:42]([NH2:44])=[NH:43])[CH:38]=[CH:39][CH:40]=1)([O-:34])=[O:33]>C1(C)C=CC=CC=1.CCOC(C)=O.CN(C=O)C>[N+:32]([C:35]1[CH:36]=[C:37]([NH:41][C:42]2[N:44]=[C:12]([C:11]3[S:10][C:9]([S:20][CH3:21])=[C:8]([C:22]#[N:23])[C:7]=3[CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[C:13]([CH3:18])=[CH:14][N:43]=2)[CH:38]=[CH:39][CH:40]=1)([O-:34])=[O:33]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 78373Dimethylformamide dimethyl acetalHCID 695552744-Cyclohexyl-5-(3-dimethylamino-2-methyl-acryloyl)-2-methylsulfanyl-thiophene-3-carbonitrileHCID 178418758HCID 178418758, Verbindung

Produkt 1

HCID 220190285-[2-(3-Nitrophenylamino)-5-methyl-pyrimidin-4-yl]-4-cyclohexyl-2-methylsulfanyl-thiophene-3-carbonitrileAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1140
Toluene
Lösungsmittel
HCID 6228DimethylformamideLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel2×

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of 4-cyclohexyl-5-(3-dimethylamino-2-methyl-acryloyl)-2-methylsulfanyl-thiophene-3-carbonitrile (0.5 g, 1.7 mmol) in toluene (3 ml) was added DMF-DMA and the reaction was heated at 90° C. overnight resulting in conversion to product as determined by TLC (40% EtOAc:hexanes). The crude product was combined with DMF (10 ml) and 3-Nitrophenylguanidine (0.5 g, 2.78 mmol) in a sealed tube and heated at 120° C. overnight resulting in conversion to product as determined by TLC (40% EtOAc:hexanes). The reaction was partitioned between EtOAc and water, the organics were dried over sodium sulfate then concentrated in vacuo. The crude product was purified by chromatography (silica gel, 10% EtOAC:hexanes) to afford 0.334 g (3.05 umol) of V-7 in 42% yield for 2 steps. 1H NMR (CDCl3) δ1.0-2.0 (m, 10H), 2.1 (s, 3H), 2.6(s, 3H), 7.4(m, 1H), 7.7 (d, 1H), 7.8 (d, 1H), 8.3 (s, 1H), 8.7 (s, 1H).

Aufarbeitung

  1. customresulting in conversion to product
  2. temperatureheated at 120° C. overnight
  3. customresulting in conversion to product
  4. customThe reaction was partitioned between EtOAc and water
  5. dry with materialthe organics were dried over sodium sulfate
  6. concentrationthen concentrated in vacuo
  7. customThe crude product was purified by chromatography (silica gel, 10% EtOAC:hexanes)
  8. customto afford 0.334 g (3.05 umol) of V-7 in 42% yield for 2 steps

Quellen und Nachweise

ORD-Eintrag
ord-6b13f0f56ddc4635806ba795084de9b6
Quelldatensatz
uspto-grants-2003_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06642227B2

Notizen zur Reaktion

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