Diisopropylethylamine → HCID 178433070, Verbindung

HRID 472247

Reaktionsgleichung

[Br:1][C:2]1[C:3](Cl)=[N:4][C:5]([N:9]2[C:13]([CH3:14])=[CH:12][CH:11]=[C:10]2[CH3:15])=[N:6][C:7]=1[CH3:8].Cl.[NH2:18][C@@H:19]1[CH2:24][CH2:23][C@H:22]([OH:25])[CH2:21][CH2:20]1.C(N(C(C)C)CC)(C)C>CC(N(C)C)=O>[Br:1][C:2]1[C:3]([NH:18][C@@H:19]2[CH2:24][CH2:23][C@H:22]([OH:25])[CH2:21][CH2:20]2)=[N:4][C:5]([N:9]2[C:13]([CH3:14])=[CH:12][CH:11]=[C:10]2[CH3:15])=[N:6][C:7]=1[CH3:8]

Komponenten

Reaktionsbedingungen

Temperatur: 160 °C

Versuchsvorschrift

A mixture of 5-bromo-4-chloro-2-(2,5-dimethyl-1H-pyrrol-1-yl)-6-methylpyrimidine (5.00 g, 17.0 mmol), cis-4-aminocyclohexanol hydrochloride (2.77 g, 18.3 mmol), and diisopropylethyl amine (8.69 mL, 49.9 mmol) in dimethylacetamide (60.0 mL) was heated at 160° C. in a sealed tube overnight. The reaction mixture was concentrated and the residue was purified by flash chromatography eluting with chloroform/methanol (0-3%). Combined fractions containing the desired product were concentrated. The resulting gum was dissolved in methyl tert-butyl ether (450 mL) and the solution was washed with 50% brine, dried (MgSO4), filtered and concentrated to afford the title compound as a orange foamy solid (5.53 g, 88%).

Aufarbeitung

concentrationThe reaction mixture was concentrated
customthe residue was purified by flash chromatography
washeluting with chloroform/methanol (0-3%)
additionCombined fractions containing the desired product
concentrationwere concentrated
dissolutionThe resulting gum was dissolved in methyl tert-butyl ether (450 mL)
washthe solution was washed with 50% brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-70c613e59907481fa3c8166fd15fbf30
Quelldatensatz: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08633204B2

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