Diisopropylethylamine → N-[(1S)-2,3-Dihydro-1H-inden-1-yl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine

HRID 222147Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 222147
Cl[C:2]1[N:7]=[CH:6][NH:5][C:4]2=[N:8][CH:9]=[CH:10][C:3]=12.C(N(CC)C(C)C)(C)C.[NH2:20][C@@H:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:23][CH2:22]1>C(O)CCC>[C@@H:21]1([NH:20][C:2]2[C:3]3[CH:10]=[CH:9][NH:8][C:4]=3[N:5]=[CH:6][N:7]=2)[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:23][CH2:22]1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 70000841-Aminoindane, (S)-HCID 178418725HCID 178418725, Verbindung

Produkt 1

HCID 58944690N-[(1S)-2,3-Dihydro-1H-inden-1-yl]-7H-pyrrolo[2,3-d]pyrimidin-4-amineAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Versuchsvorschrift

4-Chloro-1H-pyrrolo[2,3-d]pyrimidine (2.10 g, 13.6 mmol) was dissolved in 1-butanol (60.0 mL) and N,N-diisopropylethylamine (3.57 mL, 20.5 mmol) was added followed by (S)-(+)-1-aminoindan (1.93 mL, 15.0 mmol). The mixture was heated to reflux for 60 h, cooled down to rt and the solvent was evaporated to dryness. The residue was purified via silica gel chromatography eluting with a gradient of 0 to 100% EtOAc in DCM to afford the title compound (2.72 g, 80%). LC/MS: Rt=1.42 min, ES+ 251 (AA standard).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 60 h
  3. customthe solvent was evaporated to dryness
  4. customThe residue was purified via silica gel chromatography
  5. washeluting with a gradient of 0 to 100% EtOAc in DCM

Quellen und Nachweise

ORD-Eintrag
ord-b34d0fdc6da043f3bf694db8c1f584dd
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08207177B2

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