Tetrahydrofuran → (+)-3,4-dihydro-5-methyl-2-[1-(5-methyl-1-trityl-1H-imidazol-4-yl)ethyl]pyrimido[1,6-a]indol-1(2H)-one

HRID 1646776Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1646776
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]=1[CH2:11][CH2:12][NH:13][CH:14]([C:16]1[N:17]=[CH:18][N:19]([C:22]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:20]=1[CH3:21])[CH3:15].C1CCN2C(=NCCC2)CC1.[O:52]1CCC[CH2:53]1>C(OCC)(=O)C>[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]2[C:53](=[O:52])[N:13]([CH:14]([C:16]3[N:17]=[CH:18][N:19]([C:22]([C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)([C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)[C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[C:20]=3[CH3:21])[CH3:15])[CH2:12][CH2:11][C:3]=12

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 100297853-methyl-2-[2-[[1-(5-methyl-1-trityl-1H-imidazol-4-yl)ethyl]amino]ethyl]indole

Produkt 1

HCID 10460239(+)-3,4-dihydro-5-methyl-2-[1-(5-methyl-1-trityl-1H-imidazol-4-yl)ethyl]pyrimido[1,6-a]indol-1(2H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 3-methyl-2-[2-[[1-(5-methyl-1-trityl-1H-imidazol-4-yl)ethyl]amino]ethyl]indole (262 mg), N,N'-carbonyldiimidazole (210 mg), 1.8-diazabicyclo[5.4.0]-7-undecene (84 mg) and molecular sieves (100 mg) in dry tetrahydrofuran (3 ml) was stirred at reflux for 2 hours. The reaction mixture was diluted with ethyl acetate, washed with water and brine, dried over anhydrous magnesium sulfate and evaporated in vacuo. The residue was chromatographed over silica gel (eluted with 5% methanol in chloroform) to give 3,4-dihydro-5-methyl-2-[1-(5-methyl-1-trityl-1H-imidazol-4-yl)ethyl]-pyrimido[1,6-a]indol-1(2H)-one (208 mg) as glassy solid.

Aufarbeitung

  1. temperatureat reflux for 2 hours
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was chromatographed over silica gel (eluted with 5% methanol in chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-17df407c91be428b93eabd634cd48229
Quelldatensatz
uspto-grants-1993_01
Patentnummer
US05180728

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