Triethylamine → HCID 86723431, compound

HRID 2201188Notes

Reaction equation

HRID 2201188 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.[C:21]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)(=[O:24])[NH:22][NH2:23].C(N(CC)CC)C>CCO>[CH2:26]([O:25][C:21](=[O:24])[NH:22][N:23]1[C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:9]2[C:14]([N:13]([CH3:17])[C:12](=[O:18])[N:11]([CH3:19])[C:10]2=[O:20])=[CH:15]1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 79242Benzyl carbazateHCID 9503195-Benzoyl-6-(bromomethyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione2×

Product 1

HCID 86723431HCID 86723431, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Benzoyl-6-(bromomethyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione (Intermediate C) (1.15 g, 3.41 mmol), benzyl carbazate (commercial) (2.83 g, 17.05 mmol) and triethylamine (1.426 ml, 10.23 mmol) were combined in EtOH (15 ml) and the mixture heated at reflux for 15 mins. The reaction mixture was cooled to RT and evaporated under reduced pressure. The residue was partitioned between water and DCM and the phases separated. The organic phase was passed through a hydrophobic frit and evaporated under reduced pressure. The residue was triturated with Et2O and cooled in ice until precipitation occurred. The precipitate was collected by filtration, affording the title compound as a white solid.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 15 mins
  3. customevaporated under reduced pressure
  4. customThe residue was partitioned between water and DCM
  5. customthe phases separated
  6. customevaporated under reduced pressure
  7. customThe residue was triturated with Et2O
  8. temperaturecooled in ice until precipitation
  9. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-782308b707f04b33bbfbb76890dc50ff
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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