Ethanol → HCID 59457937, compound

HRID 547527Notes

Reaction equation

HRID 547527 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([NH2:8])[N:5]=[C:4]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=2)[CH:3]=1.CCO.O>[Fe].CC(O)=O>[NH2:16][C:13]1[CH:12]=[CH:11][C:10]([NH:9][C:4]2[CH:3]=[C:2]([CH3:1])[N:7]=[C:6]([NH2:8])[N:5]=2)=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 962WaterHCID 597628266-Methyl-N4-(4-nitrophenyl)pyrimidine-2,4-diamine

Product 1

HCID 59457937HCID 59457937, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

To a refluxing suspension of amine E2 (5.46 g, 0.02 mol) in 2:1 EtOH:H2O (100 mL) were sequentially added Fe dust (4.97 g, 0.09 mol) and AcOH (2 mL, 2% v/v), and the resulting dark brown suspension was refluxed for ˜14 h. After this time, the hot reaction mixture was filtered through a pad of Celite, and solvent was removed under reduced pressure. The resulting residue was extracted with hot water, and the resulting aqueous suspension filtered through a pad of Celite. Solvent was removed under reduced pressure, and the residue extracted again with hot water. The resulting aqueous suspension was filtered through a pad of Celite. Solvent was removed to afford amine E3 as a brown-white crystalline solid (4.85 g, quantitative). 1H NMR [CD3)2SO]: 2.01 [s, 3H, ArCH3], 5.68 [s, 1H, ArNHAr], 5.88 [br s, 2H, ArNH2], 6.51 [ddd, J=9.67, 4.85, 2.94 Hz, 2H, ArH], 7.14 [d, J=8.52 Hz, 2H, ArH], 8.35 [s, 1H, ArH]. LCMS (APCI+): 216 (100%).

Workup

  1. temperaturewas refluxed for ˜14 h
  2. filtrationAfter this time, the hot reaction mixture was filtered through a pad of Celite, and solvent
  3. customwas removed under reduced pressure
  4. extractionThe resulting residue was extracted with hot water
  5. filtrationthe resulting aqueous suspension filtered through a pad of Celite
  6. customSolvent was removed under reduced pressure
  7. extractionthe residue extracted again with hot water
  8. filtrationThe resulting aqueous suspension was filtered through a pad of Celite
  9. customSolvent was removed

Sources & evidence

ORD record
ord-0a1ebaf0b87343e4934026293d355335
Source dataset
uspto-grants-2011_05
Patent number
US07939546B2

Reaction notes

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