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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1525340Generated: October 26, 2026

Triethylamine → Methyl 4-(5-(4-(4-methoxybenzyloxy)-2-(pyridin-2-yl)pyrimidin-5-yl)isoxazol-3-yl)benzoate

https://huagongshe.com/reaction/1525340

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriethylamineHCID 8471—
Reactantalpha-Chloro-4-methoxycarbonylbenzaldoximeHCID 73989494—
Reactant5-Ethynyl-4-(4-methoxybenzyloxy)-2-(pyridin-2-yl)pyrimidineHCID 89462791—
SolventTetrahydrofuranHCID 8028—
ProductMethyl 4-(5-(4-(4-methoxybenzyloxy)-2-(pyridin-2-yl)pyrimidin-5-yl)isoxazol-3-yl)benzoateHCID 8947130738.4%

Reaction Steps

To a mixture of compound 37-e (517 mg, 2.43 mmol), compound 37-j (700 mg, 2.21 mmol) in THF (5 mL) was added triethylamine (335 mg, 3.31 mmol) dropwise. The mixture was stirred overnight at room temperature. The residue obtained from removal of the solvent was purified by flash chromatography (PE:EA=1:2) to afford compound 37-k (420 mg, 38%) as a yellow solid. 1H NMR (300 MHz, CDCl3) δ 8.786 (s, 1H), 8.753-8.731 (d, J=6.6 Hz, 1H), 8.172-8.144 (d, J=8.4 Hz, 2H), 8.004-7.976 (d, J=8.4 Hz, 2H), 7.838-7.806 (m, 1H), 7.645 (s, 1H), 7.615 (s, 1H), 7.495-7.470 (s, 1H), 6.875-6.846 (d, J=8.7 Hz, 2H), 6.697-6.668 (d, J=8.7 Hz, 2H), 5.786 (s, 2H), 3.960 (s, 3H), 3.723 (s, 3H), LC-MS (ESI): 495 [M+H]+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09079930B2
Source datasetuspto-grants-2015_07
ORD IDord-e278746d7c894ed1b45d8c5de76fde90
Source noteuspto-grants-2015_07