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Water → (8-Ethyl-7-imino-6-thiophen-3-yl-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-yl)-phenylamine

HRID 3224
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 3224
[H-].[Na+].[S:3]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4]1.[CH2:11]([NH:13][C:14]1[C:19]([CH:20]=O)=[CH:18][N:17]=[C:16]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:15]=1)[CH3:12].O>C(OCCO)C>[CH2:11]([N:13]1[C:14]2[N:15]=[C:16]([NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[N:17]=[CH:18][C:19]=2[CH:20]=[C:8]([C:5]2[CH:6]=[CH:7][S:3][CH:4]=2)[C:9]1=[NH:10])[CH3:12]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 837303-ThienylacetonitrileHCID 108240804-Ethylamino-2-phenylamino-pyrimidine-5-carbaldehyde

Produkt 1

HCID 10736433(8-Ethyl-7-imino-6-thiophen-3-yl-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-yl)-phenylamineAusbeute 78,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8076
Glycol monoethyl ether
Lösungsmittel

Versuchsvorschrift

To a suspension of NaH (60% in mineral oil, 27 mg) in 5 mL of 2-ethoxyethanol was added 3-thiopheneacetonitrile (168 mg, 1.36 mmol). After stirring for 5 minutes at room temperature, 4-ethylamino-2-phenylamino-pyrimidine-5-carbaldehyde (300 mg, 1.24 mmol) was added, and the reaction heated at 120° C. for 2 hours, resulting in a dark brown solution. Upon cooling, the solution was poured into water which caused precipitation. The resulting precipitate was removed by filtration and washed with water. The crude product was purified by flash chromatography, eluting with 5% methanol/methylene chloride, followed by 10% methanol/methylene chloride. Concentration of product fractions yielded 340 mg (78%) of (8-ethyl-7-imino-6-thiophen-3-yl-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-yl)-phenylamine; mp 220°-222° C.

Aufarbeitung

  1. temperaturethe reaction heated at 120° C. for 2 hours
  2. customresulting in a dark brown solution
  3. temperatureUpon cooling
  4. customprecipitation
  5. customThe resulting precipitate was removed by filtration
  6. washwashed with water
  7. customThe crude product was purified by flash chromatography
  8. washeluting with 5% methanol/methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-5ac9e9c1c2b44b098f10a1ddc3f11428
Quelldatensatz
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05733914

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