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Allylamine → 2-Allylamino-4-cyclohexylamino-7-methylthieno[3,2-d]pyrimidine hydrochloride

HRID 1250624
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1250624
[CH2:1]([NH2:4])[CH:2]=[CH2:3].[Cl:5][C:6]1[N:7]=[C:8]([NH:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[C:9]2[S:14][CH:13]=[C:12]([CH3:15])[C:10]=2[N:11]=1>O>[ClH:5].[CH2:1]([NH:4][C:6]1[N:7]=[C:8]([NH:16][CH:17]2[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]2)[C:9]2[S:14][CH:13]=[C:12]([CH3:15])[C:10]=2[N:11]=1)[CH:2]=[CH2:3]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 7853AllylamineHCID 118220702-Chloro-4-cyclohexylamino-7-methylthieno[3,2-d]pyrimidine

Produkt 1

HCID 183263832-Allylamino-4-cyclohexylamino-7-methylthieno[3,2-d]pyrimidine hydrochlorideAusbeute 66,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

In 2.28 g (40.0 mmol) of allylamine was dissolved 250 mg (0.9 mmol) of 2-chloro-4-cyclohexylamino-7-methylthieno[3,2-d]pyrimidine, and the resulting solution was heated in a sealed tube at 140° C. for 24 hours. After the reaction mixture was cooled, 100 ml of water was added thereto, followed by extraction with ethyl acetate (20 ml×3). The organic layer was washed with 20 ml of water and dried over anhydrous sodium sulfate, and then the solvent was distilled off. The residue was purified by silica gel column chromatography and an eluate of hexane/ethyl acetate=4/1 was concentrated. To the concentrate was added a 4N hydrochloric acid-ethyl acetate solution (1 ml), and crystals thus precipitated were filtered to give 200 mg (yield: 66.7%) of the title compound.

Aufarbeitung

  1. temperatureAfter the reaction mixture was cooled
  2. extractionfollowed by extraction with ethyl acetate (20 ml×3)
  3. washThe organic layer was washed with 20 ml of water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off
  6. customThe residue was purified by silica gel column chromatography
  7. concentrationan eluate of hexane/ethyl acetate=4/1 was concentrated
  8. additionTo the concentrate was added a 4N hydrochloric acid-ethyl acetate solution (1 ml), and crystals
  9. customthus precipitated
  10. filtrationwere filtered

Quellen und Nachweise

ORD-Eintrag
ord-92acb91d9a3a42f7bc3ae08505bb0b43
Quelldatensatz
uspto-grants-2002_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06339089B2

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