5-Chloro-2-iodopyrimidine → HCID 178501091, Verbindung

To a mixture of 5-chloro-2-iodopyrimidine (0.2 g, 0.83 mmol) and methyl trans-4-acetylcyclohexanecarboxylate (0.15 g, 0.83 mmol) in THF (4 mL) was added n-butyllithium (2.5 M in hexanes, 0.33 mL, 0.83 mmol) dropwise under a nitrogen atmosphere at −78° C. The mixture was stirred at −78° C. for 2 hours, and then quenched with saturate aqueous ammonium chloride solution. The mixture was extracted with ethyl acetate, and the combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by preparative TLC to afford methyl trans-4-[1-(5-chloropyrimidin-2-yl)-1-hydroxyethyl]cyclohexanecarboxylate. MS ESI calc'd for C14H20ClN2O3 [M+H]+ 299. found 299. 1H NMR: (400 MHz, CDCl3) δ 8.67 (s, 2H), 3.63 (s, 3H), 2.22-2.16 (m, 1H), 2.07-1.97 (m, 2H), 1.86-1.83 (m, 2H), 1.52 (s, 3H), 1.46-1.19 (m, 6H).

1. customquenched with saturate aqueous ammonium chloride solution
2. extractionThe mixture was extracted with ethyl acetate
3. dry with materialthe combined organic layers were dried over sodium sulfate
4. filtrationfiltered
5. concentrationconcentrated under reduced pressure
6. customThe residue was purified by preparative TLC

ORD-Eintrag

ord-33bd3efeaafd47c2a2d71eeb70db1c7b

Quelldatensatz

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09416111B2