5-Benzoyl-6-(bromomethyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione → 6-(2-hydroxy-5-nitrophenyl)-1,3-dimethyl-5-phenyl-1Hpyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

HRID 2175474Notes

Reaction equation

HRID 2175474 reaction equation
[C:1]([C:9]1[C:10](=[O:20])[N:11]([CH3:19])[C:12](=[O:18])[N:13]([CH3:17])[C:14]=1[CH2:15]Br)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:21][C:22]1[CH:27]=[C:26]([N+:28]([O-:30])=[O:29])[CH:25]=[CH:24][C:23]=1[OH:31]>CO>[OH:31][C:23]1[CH:24]=[CH:25][C:26]([N+:28]([O-:30])=[O:29])=[CH:27][C:22]=1[N:21]1[C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:9]2[C:14]([N:13]([CH3:17])[C:12](=[O:18])[N:11]([CH3:19])[C:10]2=[O:20])=[CH:15]1

Participants

4

Reactant 2

HCID 9503195-Benzoyl-6-(bromomethyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dioneHCID 36133892-Amino-4-Nitrophenol

Product 1

HCID 469049776-(2-hydroxy-5-nitrophenyl)-1,3-dimethyl-5-phenyl-1Hpyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dioneYield 113.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a 25 mL round bottom flask was placed 4a (1.00 g, 2.97 mmol) (see Example 2 for synthesis of 4a), 2-amino-4-nitrophenol (921 mg, 5.98 mmol), and methanol (12 mL). The reaction was stirred at reflux for 5 h, then cooled in an ice bath. The precipitate was filtered and rinsed with cold methanol to give 5g (1.32 g, 94%). 1H NMR (600 MHz, DMSO-d6) δ 11.72 (s, 1H), 8.19 (d, J=2.8, 1H), 8.15 (dd, J=2.9, 9.1, 1H), 7.31-7.21 (m, 5H), 7.08 (s, 1H), 7.01 (d, J=9.1, 1H), 3.34 (s, 3H), 3.21 (s, 3H). 13C NMR (151 MHz, DMSO-d6) δ 159.26, 159.03, 150.85, 138.89, 134.18, 130.34, 129.34, 128.85, 128.14, 127.36, 126.15, 126.09, 125.45, 116.60, 105.95, 102.41, 31.52, 27.48. MS (ES+) (m/z): [M+1]+ calculated for C20H17N4O5, 393.12. found 393.02.

Workup

  1. customIn a 25 mL round bottom flask was placed
  2. temperatureat reflux for 5 h
  3. temperaturecooled in an ice bath
  4. filtrationThe precipitate was filtered
  5. washrinsed with cold methanol

Sources & evidence

ORD record
ord-17d344fa64c14a80b5ea0db0ff2ac440
Source dataset
uspto-grants-2015_06
Patent number
US09062073B2

Reaction notes

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