Hydrochloric Acid → 4-Amino-N-[4-(2-amino-6-methylpyrimidin-4-ylamino)phenyl]benzamide hydrochloride

HRID 547529Notes

Reaction equation

HRID 547529 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:26])[C:17]3[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][CH:18]=3)=[CH:11][CH:10]=2)[CH:5]=[C:4]([CH3:27])[N:3]=1.CCO.[ClH:31]>[Fe].O>[ClH:31].[NH2:23][C:20]1[CH:21]=[CH:22][C:17]([C:16]([NH:15][C:12]2[CH:11]=[CH:10][C:9]([NH:8][C:6]3[CH:5]=[C:4]([CH3:27])[N:3]=[C:2]([NH2:1])[N:7]=3)=[CH:14][CH:13]=2)=[O:26])=[CH:18][CH:19]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 59762827N-[4-(2-Amino-6-methylpyrimidin-4-ylamino)phenyl]-4-nitrobenzamide

Product 1

HCID 672000444-Amino-N-[4-(2-amino-6-methylpyrimidin-4-ylamino)phenyl]benzamide hydrochlorideYield 90%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

To a refluxing suspension of amide E4 (2.10 g, 5.77 mmol) in 2:1 EtOH:H2O (100 mL) were sequentially added Fe dust (1.29 g, 23.09 mol) and c.HCl (1-2 mL), and the resulting mixture was refluxed for 24 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 crystallized from MeOH:EtOAc to afford amine E5 (in two batches) as a cream-coloured amorphous solid (1.94 g, 90%). 1H NMR [(CD3)2SO]): 2.27 [s, 3H, ArCH3], 6.16 [br s, 2H, ArNH2], 6.75 [d, J=8.36 Hz, 2H, ArNH2], 7.74 [m, 8H, ArH], 9.90 [br s, 1H ArH], 10.55 [br s, 1H, ArNHAr], 12.58 [br s, 1H, ArC(O)NH]. LCMS (APCI+): 335 (100%).

Workup

  1. filtrationAfter this time, the hot reaction mixture was filtered through a pad of Celite, and solvent
  2. customwas removed under reduced pressure
  3. customThe resulting residue was crystallized from MeOH

Sources & evidence

ORD record
ord-f0997db9d82e4dd28ada6170d0886880
Source dataset
uspto-grants-2011_05
Patent number
US07939546B2

Reaction notes

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