Propylphosphoric anhydride → 1,3-Dimethyl-5-phenyl-7,8-dihydro-1H-pyrimido[4,5-a]pyrrolizine-2,4,9(3H)-trione

HRID 2201196Notes

Reaction equation

HRID 2201196 reaction equation
[CH3:1][N:2]1[C:7]2=[CH:8][N:9]([CH2:17][CH2:18][C:19](O)=[O:20])[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[C:6]2[C:5](=[O:22])[N:4]([CH3:23])[C:3]1=[O:24].CCCP(=O)=O>CN(C=O)C>[CH3:1][N:2]1[C:7]2=[C:8]3[N:9]([C:10]([C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=4)=[C:6]2[C:5](=[O:22])[N:4]([CH3:23])[C:3]1=[O:24])[CH2:17][CH2:18][C:19]3=[O:20]

Participants

4

Reactant 2

HCID 16167369Propylphosphoric anhydrideHCID 867234383-(1,3-Dimethyl-2,4-dioxo-5-phenyl-3,4-dihydro-1H-pyrrolo[3,4-d]pyrimidin-6(2H)-yl)propanoic acid

Product 1

HCID 867234391,3-Dimethyl-5-phenyl-7,8-dihydro-1H-pyrimido[4,5-a]pyrrolizine-2,4,9(3H)-trione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(1,3-Dimethyl-2,4-dioxo-5-phenyl-3,4-dihydro-1H-pyrrolo[3,4-d]pyrimidin-6(2H)-yl)propanoic acid (step 2) (2.11 g, 6.63 mmol) and propylphosphonic anhydride (4.34 g, 6.63 mmol) 50% in DMF was heated to 100° C. overnight. The reaction mixture was cooled to RT and the precipitate isolated using suction filtration. The isolated orange solid was washed with Et2O and dried in a vacuum oven at 50° C.

Workup

  1. customthe precipitate isolated
  2. filtrationsuction filtration
  3. washThe isolated orange solid was washed with Et2O
  4. customdried in a vacuum oven at 50° C.

Sources & evidence

ORD record
ord-c74b773f80524121ae3db851080e0d20
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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