Cyclohexanol → Cyclohexyl 2-chloro-6-(cyclohexyloxy)pyrimidine-4-carboxylate

HRID 1746671Notizen

Reaktionsgleichung

[CH:1]1([OH:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[Cl:10][C:11]1[N:16]=[C:15]([C:17]([O:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)=[O:18])[CH:14]=[C:13](Cl)[N:12]=1>C1COCC1>[Cl:10][C:11]1[N:16]=[C:15]([C:17]([O:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)=[O:18])[CH:14]=[C:13]([O:7][CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[N:12]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

A cold (0° C.) solution of cyclohexanol (2.35 ml; 22.3 mmol) was treated with sodium hydride (534 mg; 22.3 mmol) in dry THF (25 ml) and stirred for 30 min at 0° C. It was slowly added to a cooled (0° C.) solution of cyclohexyl 2,6-dichloropyrimidine-4-carboxylate (Intermediate 31, 3.50 g; 12.72 mmol) in dry THF (70 ml) and the resulting mixture was stirred at 50° C. After 4 h the reaction was treated again with a solution cyclohexanol (0.34 ml; 3.18 mmol) and sodium hydride (76.3 mg; 3.18 mmol) in dry THF (3 mL) obtained as described above and it was stirred for an additional hour. The reaction mixture was concentrated under vacuum and the residue was taken up in EtOAc and the organic layer was washed with water, then brine, dried over MgSO4, filtered off and concentrated under vacuum to afford the title compound (4.80 g, 99%) without further purification.

Aufarbeitung

additionIt was slowly added to
stirringthe resulting mixture was stirred at 50° C
customobtained
stirringwas stirred for an additional hour
concentrationThe reaction mixture was concentrated under vacuum
washthe organic layer was washed with water
dry with materialbrine, dried over MgSO4
filtrationfiltered off
concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag: ord-87b0a2e778bd45b39c6e260ca6f864eb
Quelldatensatz: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09150519B2

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