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

HRID 2175471Notes

Reaction equation

HRID 2175471 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[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>[CH3:25][N:21]1[C:22]2=[CH:23][N:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[OH:8])[C:9]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)=[C:17]2[C:18](=[O:28])[N:19]([CH3:27])[C:20]1=[O:26]

Participants

4

Reactant 2

HCID 58012-AminophenolHCID 9503195-Benzoyl-6-(bromomethyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione2×

Product 1

HCID 29130826-(2-hydroxyphenyl)-1,3-dimethyl-5-phenyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dioneYield 96.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a 25 mL round bottom was placed o-aminophenol (163 mg, 1.5 mmol) and EtOH (10 mL). The mixture was warmed until homogenous and then compound 4a (250 mg, 741 μmol) was added (see Example 2 for synthesis of 4a). The mixture was stirred vigorously at reflux during which a precipitate formed. After 1 h the mixture was cooled in an ice bath, filtered, and the precipitate washed with cold EtOH to yield 5e (248 mg, 96.4%) as a white powder. 1H NMR (600 MHz,) δ 10.02 (s, 1H), 7.29-7.26 (m, 2H), 7.24-7.17 (m, 4H), 7.10 (dd, J=1.6, 7.8, 1H), 6.96 (s, 1H), 6.90 (dd, J=1.1, 8.2, 1H), 6.77 (td, J=1.2, 7.6, 1H), 3.34 (s, 3H), 3.21 (s, 3H). 13C NMR (151 MHz, DMSO d6) δ 159.11, 152.86, 150.91, 133.81, 130.35, 129.98, 129.67, 129.13, 128.58, 127.83, 127.18, 125.95, 118.99, 116.39, 106.16, 101.88, 31.50, 27.46. MS (ES+) (m/z): [M+1]+ calculated for C20H18N3O3, 348.13. found 348.11.

Workup

  1. additionwas added
  2. temperatureat reflux during which a precipitate
  3. customformed
  4. temperatureAfter 1 h the mixture was cooled in an ice bath
  5. filtrationfiltered
  6. washthe precipitate washed with cold EtOH

Sources & evidence

ORD record
ord-7611e62d30334d71aa9b44f6f8ae2752
Source dataset
uspto-grants-2015_06
Patent number
US09062073B2

Reaction notes

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