N-(5-nitropyrimidin-2-yl)acetamide → N-(5-aminopyrimidin-2-yl)acetamide

HRID 253699Notes

Reaction equation

HRID 253699 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][C:7]([NH:10][C:11](=[O:13])[CH3:12])=[N:8][CH:9]=1)([O-])=O>CCO.[Pd]>[NH2:1][C:4]1[CH:5]=[N:6][C:7]([NH:10][C:11](=[O:13])[CH3:12])=[N:8][CH:9]=1

Participants

4

Reactant 1

HCID 45071770N-(5-nitropyrimidin-2-yl)acetamide

Product 1

HCID 20387481N-(5-aminopyrimidin-2-yl)acetamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To N-(5-nitropyrimidin-2-yl)acetamide (0.54 g, 3.0 mmol) suspended in EtOH (20 mL) under N2 was added palladium, 10 wt. % on activated carbon (0.32 g, 0.3 mmol). The reaction mixture was hydrogenated under 1 atm of H2 at RT for 2 h and then filtered through a pad of celite and washed with MeOH. The filtrate was concentrated to give N-(5-aminopyrimidin-2-yl)acetamide as a light-yellow solid. MS (ESI, pos. ion) m/z: 153 (M+1).

Workup

  1. filtrationfiltered through a pad of celite
  2. washwashed with MeOH
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-fd1f2a3caa724de3b8536cf547ac63e8
Source dataset
uspto-grants-2011_01
Patent number
US07872128B2

Reaction notes

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