Potassium Carbonate → 3-(2-Methyl-pyrimidin-5-yl)-7-oxo-9-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-non-5-enoic acid ethyl ester

HRID 2187376Notes

Reaction equation

COP([CH2:7][C:8](=[O:21])[CH2:9][CH2:10][C:11]1[CH:20]=[CH:19][C:18]2[CH2:17][CH2:16][CH2:15][NH:14][C:13]=2[N:12]=1)(=O)OC.[CH2:22]([O:24][C:25](=[O:38])[CH2:26][CH:27]([C:31]1[CH:32]=[N:33][C:34]([CH3:37])=[N:35][CH:36]=1)[CH2:28][CH:29]=O)[CH3:23].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:22]([O:24][C:25](=[O:38])[CH2:26][CH:27]([C:31]1[CH:32]=[N:33][C:34]([CH3:37])=[N:35][CH:36]=1)[CH2:28][CH:29]=[CH:7][C:8](=[O:21])[CH2:9][CH2:10][C:11]1[CH:20]=[CH:19][C:18]2[CH2:17][CH2:16][CH2:15][NH:14][C:13]=2[N:12]=1)[CH3:23]

Participants

Conditions

Temperature: 50 °C

Procedure

To a mixture of 2-10 (100 mg, 0.42 mmol) and 2-6 (160 mg, 0.54 mmol) in DMF (3 mL) was added K2CO3 (87 mg, 0.63 mmol) followed by heating to 50° C. for 18 hours. Following evaporative removal of the solvent, the residue was chromatographed (silica gel, 70:25:5 CHCl3/EtOAc/MeOH) to give 2-11 as a clear oil.

Workup

customremoval of the solvent
customthe residue was chromatographed (silica gel, 70:25:5 CHCl3/EtOAc/MeOH)

Sources & evidence

ORD record: ord-403f0db9cca54af5af2085923d641bab
Source dataset: uspto-grants-2002_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06410526B1

Reaction notes

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