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

HRID 1912356Notes

Reaction equation

HRID 1912356 reaction equation
C(N)(=O)C.[CH3:5][N:6]1[C:11]2=[CH:12][N:13]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[NH:27]C(=O)C)[C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:10]2[C:9](=[O:31])[N:8]([CH3:32])[C:7]1=[O:33]>Cl>[NH2:27][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[N:13]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:10]2[C:11]([N:6]([CH3:5])[C:7](=[O:33])[N:8]([CH3:32])[C:9]2=[O:31])=[CH:12]1

Participants

4

Reactant 2

HCID 178AcetamideHCID 68161872N-(2-(1,3-dimethyl-2,4-dioxo-5-phenyl-3,4-dihydro-1H-pyrrolo[3,4-d]pyrimidin-6(2H)-yl)phenyl)acetamide

Product 1

HCID 7098566-(2-aminophenyl)-1,3-dimethyl-5-phenyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dioneYield 69.3%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Acetamide compound 5 (200 mg, 0.5 mmol) was refluxed in hydrochloric acid (4 N, 10 mL) for 6 h. The reaction mixture was evaporated under vacuum, and the residue was dissolved in water and neutralized to give 6 (120 mg, 67%) as a white precipitate: mp>300° C.; 1H NMR (DMSO-d6): δ 7.32-7.26 (m, 2H), 7.23-7.15 (m, 3H), 7.00 (t, 1H, J=7.32 Hz), 6.87 (s, 1H), 6.80 (d, 1H, J=7.69), 6.70 (d, 1H, J=8.06 Hz), 6.41 (t, 1H, J=7.32 Hz), 5.00 (s, 2H), 3.29 (s, 3H), 3.16 (s, 3H); MS (ES+) (m/z): [M+1]+ calculated for C20H19N4O2, 347.39. found 347.10.

Workup

  1. customThe reaction mixture was evaporated under vacuum
  2. dissolutionthe residue was dissolved in water

Sources & evidence

ORD record
ord-1b151d872beb4ef08a9f8ec8c7a08780
Source dataset
uspto-grants-2013_12
Patent number
US08609661B2

Reaction notes

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