1,2,3,4-Tetrahydroquinoline-2-carboxylic acid → Methyl 2-(1,2,3,4-tetrahydroquinolin-2-yl)-1-methyl-5-benzoyloxy-6-oxo-1,6-dihydropyrimidine-4-carboxylate

HRID 1161910Notes

Reaction equation

HRID 1161910 reaction equation
[C:1]([O:9][C:10]1[C:15](=[O:16])[N:14]([CH3:17])[C:13]([CH:18]2[CH2:27][CH2:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]2C(OCC2C=CC=CC=2)=O)=[N:12][C:11]=1[C:38]([O:40][CH3:41])=[O:39])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C2C(=CC=CC=2)CCC1C(O)=O>CCOC(C)=O.[Pd]>[NH:19]1[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:26][CH2:27][CH:18]1[C:13]1[N:14]([CH3:17])[C:15](=[O:16])[C:10]([O:9][C:1](=[O:8])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[C:11]([C:38]([O:40][CH3:41])=[O:39])[N:12]=1

Participants

5

Reactant 2

HCID 128777941,2,3,4-Tetrahydroquinoline-2-carboxylic acidHCID 66922433Benzyl 2-[5-(benzoyloxy)-4-(methoxycarbonyl)-1-methyl-6-oxo-1,6-dihydropyrimidin-2-yl]-1,2,3,4-tetrahydroquinoline-1-carboxylate

Product 1

HCID 21098173Methyl 2-(1,2,3,4-tetrahydroquinolin-2-yl)-1-methyl-5-benzoyloxy-6-oxo-1,6-dihydropyrimidine-4-carboxylate

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 23938PalladiumSolvent

Procedure

Benzyl 2-[5-(benzoyloxy)-4-(methoxycarbonyl)-1-methyl-6-oxo-1,6-dihydropyrimidin-2-yl]-1,2,3,4-tetrahydroquinoline-1-carboxylate (prepared from tetrahydroquinoline-2-carboxylic acid (Robl et al, Tetrahedron Letters 1995, 36: 1593) by protection of the nitrogen and following procedures similar to those set forth in Examples 1 or 2 in combination with a deprotection step) was dissolved in EtOAc and hydrogenated at atmospheric pressure on 10% Pd/C at room temperature overnight. The title product was obtained as the residue after filtration and evaporation of the organic solvent.

Sources & evidence

ORD record
ord-658714f8411341a6b259142f77a1de8e
Source dataset
uspto-grants-2010_10
Patent number
US07820660B2

Reaction notes

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