2-Bromo-5-chloropyrimidine → HCID 178482372, Verbindung

HRID 1743765Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1743765
[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]([Cl:20])=[CH:16][N:15]=1>>[Cl: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

3

Edukt 2

HCID 222362732-Bromo-5-chloropyrimidine2×HCID 178484802HCID 178484802, Verbindung

Produkt 1

HCID 178482372HCID 178482372, Verbindung

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

In analogy to example 1.7, trans-3-(4-Methylamino-cyclohexyl)-prop-2-yn-1-ol and 1.5 equivalent of 2-Bromo-5-chloro-pyrimidine [synthesized from 5-chloro-2-hydroxy-pyrimidine in analogy to 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] were heated for 0.5 h at 80° C., 1 h at 120° C., then 0.5 equivalent of 2-Bromo-5-chloro-pyrimidine were added and heated for 1 h at 120° C. to give after work up trans-3-{4-[(5-Chloro-pyrimidin-2-yl)-methyl-amino]-cyclohexyl}-prop-2-yn-1-ol, mp: 148–150° C., dec.; MS: 280 (MH+, 1Cl).

Quellen und Nachweise

ORD-Eintrag
ord-4de9057f37634c83b48965b52cbee0cb
Quelldatensatz
uspto-grants-2006_03
Patentnummer
US07012077B2

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