3-[(2-Amino-6-methyl-4-pyrimidinyl)amino]-N-(4-nitrophenyl)benzamide hydrochloride → 3-[(2-Amino-6-methyl-4-pyrimidinyl)amino]-N-(4-aminophenyl)benzamide hydrochloride

HRID 547542Notes

Reaction equation

HRID 547542 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]([CH3:28])[N:4]=1>[Pd].CO>[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]([NH2:22])=[CH:18][CH:17]=2)=[O:14])[CH:6]=[C:5]([CH3:28])[N:4]=1

Participants

4

Reactant 1

HCID 672005473-[(2-Amino-6-methyl-4-pyrimidinyl)amino]-N-(4-nitrophenyl)benzamide hydrochloride

Product 1

HCID 672024523-[(2-Amino-6-methyl-4-pyrimidinyl)amino]-N-(4-aminophenyl)benzamide hydrochlorideYield 58.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a suspension of compound B2 (1.41 g, 3.51 mmol) in (MeOH) 30 (mL) was added 10% Pd/C (20 mg) and hydrogenated under 45 Hg mm for 5 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 B3 (758 mg, 58%); m.p. (MeOH/EtOAc); 1H NMR [(CD3)2SO] δ12.70 (br, 1 H, NH), 10.83 (br s, 1 H, NH), 10.43 (s, 1 H, NH), 9.70 (v br, 2 H, NH2), 8.05-7.84 (br m, 2 H, ArH), 7.85-7.75 (m, 4 H, ArH & NH2), 7.55 (t, J=7.9 Hz, 1 H, ArH), 7.28 (d, J=8.7 Hz, 2 H, ArH), 6.24 (s, 1 H, ArH), 2.30 (s, 3 H, CH3); mass APCI+ 335.

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-aebe5d8150ea4e889622a84007c23712
Source dataset
uspto-grants-2011_05
Patent number
US07939546B2

Reaction notes

Loading…