4,4-Diethoxybutylamine → HCID 86723419, compound

HRID 2201296Notes

Reaction equation

HRID 2201296 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(O[CH:24](OCC)[CH2:25][CH2:26][CH2:27][NH2:28])C>CCO>[CH3:17][N:13]1[C:14]2=[C:15]3[N:28]([C:1]([C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[C:9]2[C:10](=[O:20])[N:11]([CH3:19])[C:12]1=[O:18])[CH2:27][CH2:26][CH:25]=[CH:24]3

Participants

4

Reactant 2

HCID 806724,4-DiethoxybutylamineHCID 9503195-Benzoyl-6-(bromomethyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione2×

Product 1

HCID 86723419HCID 86723419, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Benzoyl-6-(bromomethyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione (Intermediate C), (1.169 g, 3.47 mmol) in EtOH (20 mL) was treated with 4,4-diethoxybutan-1-amine (0.659 mL, 3.81 mmol) and TEA (0.966 mL, 6.93 mmol) and the mixture heated at reflux for 50 min. The reaction mixture was cooled to RT and evaporated under reduced pressure. The residue was re-dissolved in THF (20 mL), 1M hydrochloric acid (3.47 mL) was added and the mixture stirred at RT for 1.5 h. The reaction mixture was diluted with EtOAc, washed with water, brine and the organic phase was dried over sodium sulphate and evaporated under reduced pressure. The residue was triturated with DCM/hexane and the precipitate collected by filtration to give the title product as a pale pink solid.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 50 min
  3. customevaporated under reduced pressure
  4. dissolutionThe residue was re-dissolved in THF (20 mL)
  5. addition1M hydrochloric acid (3.47 mL) was added
  6. additionThe reaction mixture was diluted with EtOAc
  7. washwashed with water, brine
  8. dry with materialthe organic phase was dried over sodium sulphate
  9. customevaporated under reduced pressure
  10. customThe residue was triturated with DCM/hexane
  11. filtrationthe precipitate collected by filtration

Sources & evidence

ORD record
ord-423e8c4b44fb404785e5d55b1f5fa0fa
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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