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

HRID 3225

Reaktionsgleichung

Reaktionsgleichung von HRID 3225
[H-].[Na+].[S:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[CH2:8][C:9]#[N:10].[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:4]2[S:3][CH:7]=[CH:6][CH:5]=2)[C:9]1=[NH:10])[CH3:12]

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 728802-ThienylacetonitrileHCID 108240804-Ethylamino-2-phenylamino-pyrimidine-5-carbaldehyde

Produkt 1

HCID 11501131(8-Ethyl-7-imino-6-thiophen-2-yl-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-yl)-phenylamineAusbeute 85,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8076Glycol monoethyl etherLösungsmittel

Versuchsvorschrift

To a suspension of NaH (60% in mineral oil, 27 mg) in 5 mL of 2-ethoxyethanol was added 2-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 370 mg (85%) of (8-ethyl-7-imino-6-thiophen-2-yl-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-yl)-phenylamine; mp 204°-205° 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-231cd6e88b2340b49783a8530c5952cf
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05733914

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