5-Benzoyl-6-(bromomethyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione → HCID 51361339, compound

HRID 2175475Notes

Reaction equation

HRID 2175475 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([NH2:11])[CH:5]=1)([O-:3])=[O:2].[C:12]([C:20]1[C:21](=[O:31])[N:22]([CH3:30])[C:23](=[O:29])[N:24]([CH3:28])[C:25]=1[CH2:26]Br)(=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(O)C>[NH2:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]=1[N:11]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:20]2[C:25]([N:24]([CH3:28])[C:23](=[O:29])[N:22]([CH3:30])[C:21]2=[O:31])=[CH:26]1

Participants

4

Reactant 2

HCID 9503195-Benzoyl-6-(bromomethyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dioneHCID 51117914-Nitro-1,2-phenylenediamine

Product 1

HCID 51361339HCID 51361339, compoundYield 88.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a 25 mL round bottom flask 4-nitro 1,2-phenylenediamine (300 mg, 1.96 mmol), and 4a (330 mg, 979 mmol) (see Example 2 for synthesis of 4a) were combined in ethanol (10 mL). The stirred mixture was brought to reflux for 3 h during which a yellow precipitate formed. The mixture was then chilled in an ice bath, filtered, and the precipitate washed with cold ethanol to give 5b (340 mg, 88.7%) as a waxy shiny yellow solid; mp>300° C. 1H NMR (600 MHz, DMSO-d6) δ 7.97 (dd, J=2.7, 9.2, 1H), 7.86 (d, J=2.6, 1H), 7.37-7.32 (m, 2H), 7.28-7.24 (m, 4H), 7.05 (s, 1H), 6.75 (d, J=9.2, 1H), 6.65 (s, 2H), 3.35 (s, 3H), 3.21 (s, 3H). 13C NMR (151 MHz, DMSO-d6) δ 159.06, 151.66, 150.89, 135.01, 133.84, 130.38, 129.34, 129.02; 128.32, 127.38, 126.19, 126.05, 121.34, 114.31, 105.49, 102.98, 31.59, 27.46. MS (ES+) (m/z): [M+1]+ calculated for C20H18N5O4, 392.135880. found 392.03.

Workup

  1. temperatureto reflux for 3 h during which a yellow precipitate
  2. customformed
  3. temperatureThe mixture was then chilled in an ice bath
  4. filtrationfiltered
  5. washthe precipitate washed with cold ethanol

Sources & evidence

ORD record
ord-2d55d3919d2644dca1b390458dbdda5c
Source dataset
uspto-grants-2015_06
Patent number
US09062073B2

Reaction notes

Loading…