Triethylamine → Ethyl 5-(1,3-dimethyl-2,4-dioxo-5-phenyl-3,4-dihydro-1H-pyrrolo[3,4-d]pyrimidin-6(2H)-yl)pentanoate

HRID 2201271Notes

Reaction equation

HRID 2201271 reaction equation
[C:1]([C:9]1[C:10](=[O:20])[N:11]([CH3:19])[C:12](=[O:18])[N:13]([CH3:17])[C:14]=1[CH2:15]Br)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28].C(N(CC)CC)C>C(O)C>[CH3:17][N:13]1[C:14]2=[CH:15][N:22]([CH2:23][CH2:24][CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[C:9]2[C:10](=[O:20])[N:11]([CH3:19])[C:12]1=[O:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9503195-Benzoyl-6-(bromomethyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione2×HCID 16094861Ethyl 5-aminopentanoate hydrochloride

Product 1

HCID 86723511Ethyl 5-(1,3-dimethyl-2,4-dioxo-5-phenyl-3,4-dihydro-1H-pyrrolo[3,4-d]pyrimidin-6(2H)-yl)pentanoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Benzoyl-6-(bromomethyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione (Intermediate C) (1.38 g, 4.09 mmol), ethyl 5-aminovalerate hydrochloride (1.109 g, 6.14 mmol) and triethylamine (1.711 mL, 12.28 mmol) were combined in ethanol (20 mL) and the mixture heated at reflux for 40 mins. The reaction mixture was cooled to room temperature and evaporated under vacuum. The residue was partitioned between water and DCM and the phases separated. The organic phase was passed through a hydrophobic frit and evaporated onto silica. The silica was deposited onto a 25 g silica cartridge and the system eluted with 20% EtOAc/hexane, 40% EtOAc/hexane, 60% EtOAc/hexane and 80% EtOAc/hexane. The product fractions were combined and concentrated under reduced pressure to afford the title compound;

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 40 mins
  3. customevaporated under vacuum
  4. customThe residue was partitioned between water and DCM
  5. customthe phases separated
  6. customevaporated onto silica
  7. washthe system eluted with 20% EtOAc/hexane, 40% EtOAc/hexane, 60% EtOAc/hexane and 80% EtOAc/hexane
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f0c5311b3eda4880b77a6a6a344db360
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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