Pyridine → Methyl 5-benzoyloxy-1-methyl-6-oxo-2-[1-(pyridin-2-ylcarbonyl)-1,2,3,4-tetrahydroquinolin-2-yl]-1,6-dihydropyrimidine-4-carboxylate

HRID 1161911Notes

Reaction equation

HRID 1161911 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH:2]1[C:11]1[N:12]([CH3:31])[C:13](=[O:30])[C:14]([O:21][C:22](=[O:29])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:15]([C:17]([O:19][CH3:20])=[O:18])[N:16]=1.N1C=CC=CC=1.Cl.[N:39]1[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=1[C:45](Cl)=[O:46]>ClCCl.CN(C1C=CN=CC=1)C>[C:22]([O:21][C:14]1[C:13](=[O:30])[N:12]([CH3:31])[C:11]([CH:2]2[CH2:3][CH2:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:1]2[C:45]([C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][N:39]=2)=[O:46])=[N:16][C:15]=1[C:17]([O:19][CH3:20])=[O:18])(=[O:29])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 135033Picolinoyl Chloride HydrochlorideHCID 21098173Methyl 2-(1,2,3,4-tetrahydroquinolin-2-yl)-1-methyl-5-benzoyloxy-6-oxo-1,6-dihydropyrimidine-4-carboxylate

Product 1

HCID 17961698Methyl 5-benzoyloxy-1-methyl-6-oxo-2-[1-(pyridin-2-ylcarbonyl)-1,2,3,4-tetrahydroquinolin-2-yl]-1,6-dihydropyrimidine-4-carboxylate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

The residue of Step 1 was dissolved in dichloromethane. Pyridine, picolinoyl chloride hydrochloride and a catalytic amount of DMAP were added. A further addition of the reactants was made after two hours. After evaporation of the solvent, the residue was diluted with EtOAc, the organic phase washed with water, dried (Na2SO4) and evaporated to afford the title product.

Workup

  1. additionA further addition of the reactants
  2. customAfter evaporation of the solvent
  3. additionthe residue was diluted with EtOAc
  4. washthe organic phase washed with water
  5. dry with materialdried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-ca7992adc223445693da579f8313ecbb
Source dataset
uspto-grants-2010_10
Patent number
US07820660B2

Reaction notes

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