Ammonium Chloride → HCID 86713575, compound

HRID 2404031Notes

Reaction equation

HRID 2404031 reaction equation
Cl[C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4](Cl)[C:3]=1[C:13]1[C:22](=[O:23])[N:21]([CH3:24])[C:20]2[N:19]=[C:18]([NH:25][C:26]3[C:31]([N+:32]([O-])=O)=[CH:30][CH:29]=[CH:28][C:27]=3[CH3:35])[N:17]=[CH:16][C:15]=2[N:14]=1.[Cl-].[NH4+]>C(O)C.O.[Fe]>[NH2:32][C:31]1[CH:30]=[CH:29][CH:28]=[C:27]([CH3:35])[C:26]=1[NH:25][C:18]1[N:17]=[CH:16][C:15]2[N:14]=[C:13]([C:3]3[CH:4]=[C:5]([O:10][CH3:11])[CH:6]=[C:7]([O:8][CH3:9])[CH:2]=3)[C:22](=[O:23])[N:21]([CH3:24])[C:20]=2[N:19]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 86713573HCID 86713573, compound

Product 1

HCID 86713575HCID 86713575, compoundYield 44%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 6-(2,6-dichloro-3,5-dimethoxyphenyl)-8-methyl-2-(2-methyl-6-nitrophenylamino)pteridin-7(8H)-one (200 mg, 0.38 mmol) in ethanol (50 mL) and water (2 mL) was added iron powder (210 mg, 3.8 mmol) and ammonium chloride (450 mg, 8 mmol). The mixture was refluxed for 2 h. The solvents were evaporated, and the residue was diluted with brine and dichloromethane. The solid was filtered off, and the filtrate was extracted with dichloromethane (50 mL*6). The organic layers were combined, dried over sodium sulfate, filtered and concentrated to give the title compound (70 mg, 38%). MS (ES+) C22H20Cl2N6O3 requires: 486, 488. found: 487, 489 [M+H]+. 1H-NMR (500 MHz, CDCl3) δ ppm 8.83 (s, 1H), 7.09 (t, 1H, J=8.0 Hz), 6.74-6.71 (m, 2H), 6.65 (s, 1H), 3.94 (s, 6H), 3.85 (br. s., 2H), 3.63-3.59 (br, 3H), 2.25 (s, 3H).

Workup

  1. temperatureThe mixture was refluxed for 2 h
  2. customThe solvents were evaporated
  3. additionthe residue was diluted with brine and dichloromethane
  4. filtrationThe solid was filtered off
  5. extractionthe filtrate was extracted with dichloromethane (50 mL*6)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-7dd1573ac4c847829766d7eb1b570478
Source dataset
uspto-grants-2014_08
Patent number
US08802697B2

Reaction notes

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