4-Methoxybenzylamine → 4-chloro-7-(4-methoxybenzyl)-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine

HRID 1192425Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1192425
Cl[C:2]1[C:7]([CH2:8][CH2:9]OS(C)(=O)=O)=[C:6]([Cl:15])[N:5]=[CH:4][N:3]=1.[CH3:16][O:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][NH2:23])=[CH:20][CH:19]=1>ClCCCl>[Cl:15][C:6]1[C:7]2[CH2:8][CH2:9][N:23]([CH2:22][C:21]3[CH:24]=[CH:25][C:18]([O:17][CH3:16])=[CH:19][CH:20]=3)[C:2]=2[N:3]=[CH:4][N:5]=1

Komponenten

4

Edukt 2

HCID 754524-MethoxybenzylamineHCID 86598737Methanesulfonic acid 2-(4,6-dichloro-pyrimidin-5-yl)-ethyl ester

Produkt 1

HCID 529881474-chloro-7-(4-methoxybenzyl)-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidineAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

A solution of methanesulfonic acid 2-(4,6-dichloro-pyrimidin-5-yl)-ethyl ester (0.50 g, 1.84 mmol) and 4-methoxybenzylamine (0.60 g, 4.37 mmol) in DCE (30 mL) and TEA (4 mL) was refluxed overnight. After cooling, the solvent was removed and the residue was subject to column chromatography, eluted by hexane/ethyl acetate (4:1) to give 4-Chloro-7-(4-methoxy-benzyl)-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine (0.36 g, 71%). 1H NMR (CDCl3, 400 MHz) δ 8.35 (s, 1H), 7.26 (dd, J=2.8 Hz, J=1.6 Hz, 2H), 6.88 (d, J=4.4 Hz, 2H), 5.33 (s, 1H), 4.62 (d, J=5.6 Hz, 2H), 3.81 (s, 3H), 3.73 (t, J=7.2 Hz, 2H), 3.04 (t, J=6.8 Hz, 2H). MS (APCI+) [M+H]+276.

Aufarbeitung

  1. temperatureAfter cooling
  2. customthe solvent was removed
  3. washeluted by hexane/ethyl acetate (4:1)

Quellen und Nachweise

ORD-Eintrag
ord-72c4bdf021f74e1fbd53b37ac7d7140e
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08680114B2

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