Ethyl Acetate → 5-amino-N-(2-aminopyrimidin-5-yl)-2-methylbenzamide

HRID 453354Notes

Reaction equation

HRID 453354 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([NH:8][C:9](=[O:20])[C:10]2[CH:15]=[C:14]([N+:16]([O-])=O)[CH:13]=[CH:12][C:11]=2[CH3:19])=[CH:4][N:3]=1.CCOC(C)=O>[Pd].CO>[NH2:16][C:14]1[CH:13]=[CH:12][C:11]([CH3:19])=[C:10]([CH:15]=1)[C:9]([NH:8][C:5]1[CH:6]=[N:7][C:2]([NH2:1])=[N:3][CH:4]=1)=[O:20]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 16118604N-(2-aminopyrimidin-5-yl)-2-methyl-5-nitrobenzamide

Product 1

HCID 161168485-amino-N-(2-aminopyrimidin-5-yl)-2-methylbenzamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A round bottom flask equipped with a stir bar was charged with N-(2-aminopyrimidin-5-yl)-2-methyl-5-nitrobenzamide 8 (300 mg, 1.1 mmol), 10% Pd/C (˜150 mg), EtOAc (24 mL) and MeOH (6 mL). The mixture was purged with H2 (3× evacuation and back-fill cycles) then allowed to stir under an H2 balloon. After 24 h, TLC and LCMS indicated that the starting material was completely consumed. The mixture was filtered through a pad of Celite, washing with MeOH and CH2Cl2. Recrystallization from MeOH/CH2Cl2 afforded 5-amino-N-(2-aminopyrimidin-5-yl)-2-methylbenzamide 9 as a pale yellow crystalline solid.

Workup

  1. customA round bottom flask equipped with a stir bar
  2. customThe mixture was purged with H2 (3× evacuation and back-fill cycles)
  3. customwas completely consumed
  4. filtrationThe mixture was filtered through a pad of Celite
  5. washwashing with MeOH and CH2Cl2
  6. customRecrystallization from MeOH/CH2Cl2

Sources & evidence

ORD record
ord-585ad0208dba42d6a6d7e89a63403fab
Source dataset
uspto-grants-2013_07
Patent number
US08492404B2

Reaction notes

Loading…