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

HRID 2175470Notes

Reaction equation

HRID 2175470 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[C:9]([C:17]1[C:18](=[O:28])[N:19]([CH3:27])[C:20](=[O:26])[N:21]([CH3:25])[C:22]=1[CH2:23]Br)(=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CCO>[NH2:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[N:8]1[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:17]2[C:22]([N:21]([CH3:25])[C:20](=[O:26])[N:19]([CH3:27])[C:18]2=[O:28])=[CH:23]1

Participants

4

Reactant 2

HCID 7243O-PhenylenediamineHCID 9503195-Benzoyl-6-(bromomethyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione

Product 1

HCID 7098566-(2-aminophenyl)-1,3-dimethyl-5-phenyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dioneYield 96.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

1,2-Phenylenediamine (1.320 g, 12.2 mmol) in absolute EtOH (25 mL) was stirred in a 50 mL round bottom flask. The mixture was warmed on an oil bath until homogenous, and then 4a (2.055 g, 6.1 mmol) was added with the aid of a powder funnel and EtOH (5 mL). The solution was stirred vigorously at refluxed for 1 h, during which a white precipitate formed. The reaction was then cooled in an ice bath, filtered, and the precipitate washed with cold ethanol to yield 5a (2.0357 g, 96.5%) as a white powder. 1H NMR (600 MHz, DMSO-d6) δ 7.37-7.31 (m, 2H), 7.25-7.19 (m, 3H), 7.08-7.02 (m, 1H), 6.92 (s, 1H), 6.83 (dd, J=1.3, 7.8, 1H), 6.75 (d, J=8.1, 1H), 6.48-6.43 (m, 1H), 5.08 (s, 2H), 3.33 (s, 3H), 3.19 (s, 3H). 13C NMR (151 MHz, DMSO-d6) δ 159.07, 150.89, 144.76, 133.51, 130.42, 129.49, 129.36, 129.05, 128.64, 127.89, 127.13, 123.10, 115.65, 115.46, 105.49, 102.23, 31.50, 27.40. MS (ES+) (m/z): [M+1]+ calculated for C20H19N4O2, 347.39. found 347.05.

Workup

  1. additionwas added with the aid of a powder funnel
  2. temperatureat refluxed for 1 h, during which a white precipitate
  3. customformed
  4. temperatureThe reaction was then cooled in an ice bath
  5. filtrationfiltered
  6. washthe precipitate washed with cold ethanol

Sources & evidence

ORD record
ord-61936d395a0d4d328e67de1a8a1a3b91
Source dataset
uspto-grants-2015_06
Patent number
US09062073B2

Reaction notes

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