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

HRID 1482879Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[N:4][C:5](I)=[N:6][CH:7]=1.[C:9]([C@H:12]1[CH2:17][CH2:16][C@H:15]([C:18]([O:20][CH3:21])=[O:19])[CH2:14][CH2:13]1)(=[O:11])[CH3:10].C([Li])CCC>C1COCC1>[Cl:1][C:2]1[CH:3]=[N:4][C:5]([C:9]([C@H:12]2[CH2:17][CH2:16][C@H:15]([C:18]([O:20][CH3:21])=[O:19])[CH2:14][CH2:13]2)([OH:11])[CH3:10])=[N:6][CH:7]=1

Participants

Conditions

Temperature: -78 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-33bd3efeaafd47c2a2d71eeb70db1c7b
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09416111B2

Reaction notes

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