Dimethylformamide → 1,3-Dimethyl-2,4-dioxo-5-phenyl-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidine-7-carbaldehyde

HRID 2201311Notes

Reaction equation

HRID 2201311 reaction equation
P(Cl)(Cl)(Cl)=O.[CH3:6][N:7]1[C:12]2=[CH:13][NH:14][C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:11]2[C:10](=[O:22])[N:9]([CH3:23])[C:8]1=[O:24].CN([CH:28]=[O:29])C>>[CH3:6][N:7]1[C:12]2=[C:13]([CH:28]=[O:29])[NH:14][C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:11]2[C:10](=[O:22])[N:9]([CH3:23])[C:8]1=[O:24]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 167636451,3-dimethyl-5-phenyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

Product 1

HCID 867235421,3-Dimethyl-2,4-dioxo-5-phenyl-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidine-7-carbaldehyde

Conditions

Temperature
0 °C

Procedure

Phosphorous oxychloride (1.081 mL, 11.60 mmol) was added slowly to a solution of 1,3-dimethyl-5-phenyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione (2.96 g, 11.60 mmol) in DMF (40 mL) at 0° C. The mixture was stirred at 0° C. for 15 mins. The reaction was quenched with 2M HCl(aq), diluted with EtOAc, and the mixture stirred overnight. The mixture was then extracted with EtOAc (3×) and the combined organic phases washed with brine, dried over sodium sulphate and evaporated under vacuum. The residue was triturated with diethyl ether/hexane to afford the title compound.

Workup

  1. customThe reaction was quenched with 2M HCl(aq)
  2. additiondiluted with EtOAc
  3. stirringthe mixture stirred overnight
  4. extractionThe mixture was then extracted with EtOAc (3×)
  5. washthe combined organic phases washed with brine
  6. dry with materialdried over sodium sulphate
  7. customevaporated under vacuum
  8. customThe residue was triturated with diethyl ether/hexane

Sources & evidence

ORD record
ord-2f85d8f4a9db40a3b4a53dd8ae6b7e7e
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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