Ethyl 4-piperidinecarboxylate → HCID 59845595, compound

HRID 1253831Notes

Reaction equation

HRID 1253831 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N:9]2[C:13]3[N:14]=[C:15]([CH3:19])[N:16]=[C:17](Cl)[C:12]=3[CH:11]([CH3:20])[C:10]2=[O:21])=[C:4]([CH3:22])[CH:3]=1.[NH:23]1[CH2:33][CH2:32][CH:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:25][CH2:24]1.C(N(CC)C(C)C)(C)C>C(O)C>[CH2:30]([O:29][C:27]([CH:26]1[CH2:32][CH2:33][N:23]([C:17]2[C:12]3[CH:11]([CH3:20])[C:10](=[O:21])[N:9]([C:5]4[C:6]([CH3:8])=[CH:7][C:2]([Br:1])=[CH:3][C:4]=4[CH3:22])[C:13]=3[N:14]=[C:15]([CH3:19])[N:16]=2)[CH2:24][CH2:25]1)=[O:28])[CH3:31]

Participants

5

Reactant 3

HCID 70770Ethyl 4-piperidinecarboxylateHCID 81531DiisopropylethylamineHCID 600353827-(4-Bromo-2,6-dimethylphenyl)-4-chloro-2,5-dimethyl-5,7-dihydropyrrolo[2,3-d]pyrimidin-6-one

Product 1

HCID 59845595HCID 59845595, compoundYield 77.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 7-(4-bromo-2,6-dimethylphenyl)-4-chloro-2,5-dimethyl-5,7-dihydropyrrolo[2,3-d]pyrimidin-6-one (7.5 g), ethyl isonipecotate (4.7 g), N,N-diisopropylethylamine (3.8 g) in ethanol (35 mL) was heated at reflux for 12 hours. The reaction mixture was stirred at room temperature to afford a solid. The solid was collected by filtration and washed with cold ethanol to give 1-[7-(4-bromo-2,6-dimethylphenyl)-2,5-dimethyl-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl]piperidine-4-carboxylic acid ethyl ester (7.7 g).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 12 hours
  3. customto afford a solid
  4. filtrationThe solid was collected by filtration
  5. washwashed with cold ethanol

Sources & evidence

ORD record
ord-5b0032efdbc74802a432147ea5b7de68
Source dataset
uspto-grants-2013_06
Patent number
US08455511B2

Reaction notes

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