Triethylamine → 1,3-dimethyl-5-phenyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

HRID 2201310Notes

Reaction equation

HRID 2201310 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[Si](C)(C)[NH:23][Si](C)(C)C.C(N(CC)CC)C>O1CCOCC1.CCOC(C)=O>[CH3:17][N:13]1[C:14]2=[CH:15][NH:23][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

6

Reactant 3

HCID 8471Triethylamine2×HCID 13838Hexamethyldisilazane2×HCID 9503195-Benzoyl-6-(bromomethyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione2×

Product 1

HCID 167636451,3-dimethyl-5-phenyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

5-Benzoyl-6-(bromomethyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione 13.4a (Intermediate C) (2.33 g, 6.91 mmol), hexamethyldisilazane (2.90 mL, 13.82 mmol) and triethylamine (2.89 mL, 20.73 mmol) were combined in dioxane (20 mL) and the mixture heated at reflux for 22 hours. Further portions of hexamethyldisilazane (2.90 mL, 13.82 mmol) and triethylamine (2.89 mL, 20.73 mmol) were added to allow the reaction to run to completion. The reaction mixture was cooled to room temperature, diluted with EtOAc (150 mL) and washed with 1M HCl (aq) and brine. The organic phases was dried over sodium sulphate and evaporated under vacuum. The residue was triturated with DCM/diethyl ether/hexane to afford the title compound.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 22 hours
  3. customthe reaction
  4. washwashed with 1M HCl (aq) and brine
  5. dry with materialThe organic phases was dried over sodium sulphate
  6. customevaporated under vacuum
  7. customThe residue was triturated with DCM/diethyl ether/hexane

Sources & evidence

ORD record
ord-aae9d0f600564a41ab68824d59d92f96
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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