Diisopropylethylamine → HCID 178482349, Verbindung

HRID 1743764Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1743764
[CH3:1][NH:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]#[C:10][CH2:11][OH:12])[CH2:5][CH2:4]1.Br[C:14]1[N:19]=[CH:18][C:17]([Br:20])=[CH:16][N:15]=1.C(N(C(C)C)C(C)C)C>>[Br:20][C:17]1[CH:16]=[N:15][C:14]([N:2]([CH3:1])[C@H:3]2[CH2:4][CH2:5][C@H:6]([C:9]#[C:10][CH2:11][OH:12])[CH2:7][CH2:8]2)=[N:19][CH:18]=1

Komponenten

4

Edukt 3

HCID 81531DiisopropylethylamineHCID 109555882,5-DibromopyrimidineHCID 178484802HCID 178484802, Verbindung

Produkt 1

HCID 178482349HCID 178482349, VerbindungAusbeute 73 %

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 0.51 g (3.05 mmol) trans-3-(4-Methylamino-cyclohexyl)-prop-2-yn-1-ol, 0.87 g (3.66 mmol) 2,5-dibromo-pyrimidine [Brown, Desmond J.; Arantz, B. W., Pyrimidine reactions. XXII. Relative reactivities of corresponding chloro-, bromo-, and iodopyrimidines in aminolysis. J. Chem. Soc. C (1971), Issue 10, 1889–91] and 1.78 ml (10.34 mmol) N-ethyldiisopropylamine was heated for 2.5 h at 80° C. The reaction was cooled, evaporated and partitioned between aqueous saturated NaHCO3/Et2O (3×). The organic phases were washed with aqueous 10% NaCl, dried (NaSO4) and evaporated. Flash chromatography on silica gel (hexane/EtOAc 95:5) gave 0.72 g (73%) of trans-3-{4-[(5-Bromo-pyrimidin-2-yl)-methyl-amino]-cyclohexyl}-prop-2-yn-1-ol, mp: 156–157° C.; MS: 324 (MH+, 1Br).

Aufarbeitung

  1. temperatureThe reaction was cooled
  2. customevaporated
  3. custompartitioned between aqueous saturated NaHCO3/Et2O (3×)
  4. washThe organic phases were washed with aqueous 10% NaCl
  5. dry with materialdried (NaSO4)
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-10831bcd3bc84b5a967ede0d67915f49
Quelldatensatz
uspto-grants-2006_03
Patentnummer
US07012077B2

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