Diisopropylethylamine → 3-Bromo-7-(1-methyl-1-triethylsilanyloxyethyl)imidazo[1,2-alpha]pyrimidine

HRID 2184004Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2184004
FC(F)(F)S([O:6][Si:7]([CH2:12][CH3:13])([CH2:10][CH3:11])[CH2:8][CH3:9])(=O)=O.[Br:16][C:17]1[N:21]2[CH:22]=[CH:23][C:24]([C:26](O)([CH3:28])[CH3:27])=[N:25][C:20]2=[N:19][CH:18]=1.C(N(CC)C(C)C)(C)C>ClCCl>[Br:16][C:17]1[N:21]2[CH:22]=[CH:23][C:24]([C:26]([CH3:28])([O:6][Si:7]([CH2:12][CH3:13])([CH2:10][CH3:11])[CH2:8][CH3:9])[CH3:27])=[N:25][C:20]2=[N:19][CH:18]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 2733308Triethylsilyl trifluoromethanesulphonateHCID 112422822-(3-Bromoimidazo[1,2-a]pyrimidin-7-yl)propan-2-ol

Produkt 1

HCID 695598483-Bromo-7-(1-methyl-1-triethylsilanyloxyethyl)imidazo[1,2-alpha]pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
-50 °C

Versuchsvorschrift

Triethylsilyl trifluoromethanesulfonate (4.85 ml, 21.5 mmol) was added dropwise over 15 min to a cooled (−50° C.) solution of 2-(3-bromoimidazo[1,2-α]pyrimidin-7-yl)propan-2-ol (5.0 g, 19.5 mmol) and N,N-diisopropylethylamine (4.76 ml, 27.5 mmol) in dichloromethane (150 ml). The mixture was stirred at −50° C. for 20 min then allowed to warm to ambient temperature over 10 h. The reaction mixture was diluted with dichloromethane (100 ml) and washed with 1N hydrochloric acid (100 ml) and water (100 ml), dried over anhydrous magnesium sulfate, filtered and evaporated. The resulting red oil was purified by dry flash column chromatography on silica eluting with dichloromethane on a gradient of methanol (0-3%) to give 3-bromo-7-(1-methyl-1-triethylsilanyloxyethyl)imidazo[1,2-α]pyrimidine as a pale yellow oil which crystallised on standing (6.21 g, 86%): δH (400 MHz, CDCl3) 0.64 (6H, q, J 8), 0.97 (9H, t, J 8), 7.50 (1H, d, J 7), 7.72 (1H, s), 8.35 (1H, d, J 7), 10.36 (1H, d, J 7); m/z (ES+) 358 (M++H).

Aufarbeitung

  1. temperatureto warm to ambient temperature over 10 h
  2. washwashed with 1N hydrochloric acid (100 ml) and water (100 ml)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe resulting red oil was purified
  7. dry with materialby dry flash column chromatography on silica eluting with dichloromethane on a gradient of methanol (0-3%)

Quellen und Nachweise

ORD-Eintrag
ord-accfb6df3ec84c2d993e4838577bd4f1
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06900215B2

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