Ammonium Chloride → HCID 178501140, compound

HRID 1482887Notes

Reaction equation

[CH:1]([C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([O:11][CH3:12])=[O:10])[CH2:5][CH2:4]1)=[O:2].[Cl:13][C:14]1[CH:15]=[N:16][C:17](I)=[N:18][CH:19]=1.C([Li])CCC.[Cl-].[NH4+]>C1COCC1>[Cl:13][C:14]1[CH:15]=[N:16][C:17]([CH:1]([OH:2])[C@H:3]2[CH2:4][CH2:5][C@H:6]([C:9]([O:11][CH3:12])=[O:10])[CH2:7][CH2:8]2)=[N:18][CH:19]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a mixture of methyl trans-4-formylcyclohexanecarboxylate (150 mg, 0.88 mmol) and 5-chloro-2-iodopyrimidine (210 mg, 0.88 mmol) in THF (4 mL) at −78° C. was added n-butyllithium (2.5 M in hexanes, 0.35 mL, 0.88 mmol) dropwise. The reaction mixture was stirred at −78° C. for 2 hours and then saturated aqueous ammonium chloride solution was added. 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 prep-TLC (ethyl acetate/petroleum ether) to afford methyl trans-4-[(5-chloropyrimidin-2-yl)(hydroxy)methyl]cyclohexanecarboxylate. MS ESI calc'd for C13H18ClN2O3 [M+H]+ 285. found 285. 1H NMR: (400 MHz, CDCl3) δ 8.70 (s, 2H), 4.68 (s, 1H), 3.65 (s, 3H), 2.24 (s, 1H), 2.03-1.82 (m, 3H), 1.48-1.42 (m, 3H), 1.31-1.27 (m, 3H).

Workup

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 prep-TLC (ethyl acetate/petroleum ether)

Sources & evidence

ORD record: ord-fbbdf7a5a0bc4169970db706970a3b2f
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09416111B2

Reaction notes

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