5-Benzoyl-6-(bromomethyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione → HCID 51361338, compound

HRID 2175476Notes

Reaction equation

HRID 2175476 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]([Cl:28])[C:25]([N+:29]([O-:31])=[O:30])=[CH:24][C:23]=1[OH:32]>C(O)C>[Cl:28][C:26]1[C:25]([N+:29]([O-:31])=[O:30])=[CH:24][C:23]([OH:32])=[C:22]([N:21]2[C:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[C:9]3[C:14]([N:13]([CH3:17])[C:12](=[O:18])[N:11]([CH3:19])[C:10]3=[O:20])=[CH:15]2)[CH:27]=1

Participants

4

Reactant 2

HCID 9503195-Benzoyl-6-(bromomethyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dioneHCID 38948482-Amino-4-chloro-5-nitrophenol

Product 1

HCID 51361338HCID 51361338, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a 10 mL round bottom flask was placed 4a (200 mg, 595 mmol) (see Example 2 for synthesis of 4a), 2-amino-4-chloro-5-nitrophenol (236 mg, 1.25 mmol), and ethanol (5 mL). The reaction was stirred at reflux for 5 h, then cooled and placed in a freezer. After several hours yellow crystals formed, which were filtered and rinsed with cold ethanol to give 5f (225 mg, 89%). 1H NMR (600 MHz, DMSO-d6) δ 11.33 (s, 1H), 7.79 (s, 1H), 7.44 (s, 1H), 7.30 (s, 5H), 7.10 (s, 1H), 3.33 (s, 3H), 3.20 (s, 3H). 13C NMR (151 MHz, DMSO-d6) δ 158.98, 152.39, 150.82, 147.31, 134.14, 131.79, 130.50, 130.32, 129.23, 128.96, 128.33, 127.48, 113.90, 112.93, 105.91, 102.66, 31.55, 27.51. MS (ES+) (m/z): [M+1]+ calculated for C20H16ClN4O5, 427.08. found 427.12.

Workup

  1. customIn a 10 mL round bottom flask was placed
  2. temperatureat reflux for 5 h
  3. temperaturecooled
  4. customAfter several hours yellow crystals formed
  5. filtrationwhich were filtered
  6. washrinsed with cold ethanol

Sources & evidence

ORD record
ord-2a47f8dba6a647efad140bc216b10577
Source dataset
uspto-grants-2015_06
Patent number
US09062073B2

Reaction notes

Loading…