3-[(2,6-Diamino-4-pyrimidinyl)amino]-N-(4-nitrophenyl)benzamide hydrochloride → N-(4-Aminophenyl)-3-[(2,6-diamino-4-pyrimidinyl)amino]benzamide hydrochloride

HRID 547544Notes

Reaction equation

HRID 547544 reaction equation
[ClH:1].[NH2:2][C:3]1[N:8]=[C:7]([NH:9][C:10]2[CH:11]=[C:12]([CH:25]=[CH:26][CH:27]=2)[C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=2)=[O:14])[CH:6]=[C:5]([NH2:28])[N:4]=1>[Pd].CO>[ClH:1].[NH2:22][C:19]1[CH:20]=[CH:21][C:16]([NH:15][C:13](=[O:14])[C:12]2[CH:25]=[CH:26][CH:27]=[C:10]([NH:9][C:7]3[CH:6]=[C:5]([NH2:28])[N:4]=[C:3]([NH2:2])[N:8]=3)[CH:11]=2)=[CH:17][CH:18]=1

Participants

4

Reactant 1

HCID 671985913-[(2,6-Diamino-4-pyrimidinyl)amino]-N-(4-nitrophenyl)benzamide hydrochloride

Product 1

HCID 67200187N-(4-Aminophenyl)-3-[(2,6-diamino-4-pyrimidinyl)amino]benzamide hydrochlorideYield 76%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a suspension of compound B5 (567 mg, 1.41 mmol) in (MeOH) (30 mL) was added 10% Pd/C (20 mg) and hydrogenated under 40 Hg mm for 6 h. The reaction mixture was filtered through a pad of celite and the filtrate was evaporated to dryness. The residue was dissolved in a small volume of MeOH then 1 ml of 1.25M HCl in MeOH was added, stirred 10 min and evaporated to dryness. The residue was recrystallized from MeOH/EtOAc to give B6 (398 mg, 76%); mp (MeOH/EtOAc)>300° C., 1H NMR [(CD3)2SO] δ10.37 (s, 1 H, NH), 9.93 (s, 1 H, NH), 7.92-7.80 (m, 4 H, ArH & NH2), 7.68 (d, J=7.7 Hz, 1 H, ArH), 7.61 (br s, 2 H, NH2), 7.49-7.45 (m, 3 H, ArH), 7.24 (br d, J=8.7 Hz, 2 H, ArH), 5.45 (s, 1 H, ArH), mass APCI+ 336.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. customthe filtrate was evaporated to dryness
  3. dissolutionThe residue was dissolved in a small volume of MeOH
  4. addition1 ml of 1.25M HCl in MeOH was added
  5. customevaporated to dryness
  6. customThe residue was recrystallized from MeOH/EtOAc

Sources & evidence

ORD record
ord-9f4f892a30bd4b5aab5771c2694dc097
Source dataset
uspto-grants-2011_05
Patent number
US07939546B2

Reaction notes

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