Diisopropylethylamine → HCID 178456860, Verbindung

HRID 58230

Reaktionsgleichung

Reaktionsgleichung von HRID 58230
Br[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][NH:6]2.[NH2:11][CH:12]([C:15]1[N:16]=[C:17]2[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[N:18]2[C:19](=[O:22])[C:20]=1[I:21])[CH2:13][CH3:14].C(N(CC)C(C)C)(C)C>C(O)C>[I:21][C:20]1[C:19](=[O:22])[N:18]2[C:23]([CH3:27])=[CH:24][CH:25]=[CH:26][C:17]2=[N:16][C:15]=1[CH:12]([NH:11][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][NH:6]2)[CH2:13][CH3:14]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 668638382-(1-aminopropyl)-3-iodo-6-methyl-4H-pyrido[1,2-a]pyrimidin-4-oneHCID 178419477HCID 178419477, Verbindung

Produkt 1

HCID 178456860HCID 178456860, VerbindungAusbeute 82,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 6-bromo-9H-purine (1.65 g, 0.008270 mol), 2-(1-aminopropyl)-3-iodo-6-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (2.58 g, 0.00752 mol), and N,N-diisopropylethylamine (1.571 mL, 0.009022 mol) in ethanol (60 mL) was refluxed under nitrogen overnight. The mixture was concentrated and the resulting residue was purified on silica gel, eluting with 0 to 10% methanol in methylene chloride, to provide the desired product (2.86 g, 82.5%). LCMS calculated for C17H17IN7O (M+H)+: m/z=462.1. Found: 462.2. 1H NMR (DMSO-d6, 300 MHz) δ 8.31 (2H, m), 8.19 (1H, s), 8.15 (1H, s), 7.69 (1H, dd, J=8.7 and 6.9 Hz), 7.44 (1H, d, J=8.7 Hz), 6.99 (1H, d, J=6.9 Hz), 5.69 (1H, m), 2.89 (3H, s), 1.91 (2H, m), 0.95 (3H, t, J=7.2 Hz) ppm.

Aufarbeitung

  1. temperaturewas refluxed under nitrogen overnight
  2. concentrationThe mixture was concentrated
  3. customthe resulting residue was purified on silica gel
  4. washeluting with 0 to 10% methanol in methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-f03b1f76545f415dbf65e04b32ec9a97
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434746B2

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