Acetic Anhydride → N-(5-nitropyrimidin-2-yl)acetamide

HRID 253698

Reaction equation

HRID 253698 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[C:11](OC(=O)C)(=[O:13])[CH3:12]>C1(C)C=CC=CC=1>[N+:8]([C:5]1[CH:4]=[N:3][C:2]([NH:1][C:11](=[O:13])[CH3:12])=[N:7][CH:6]=1)([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 7918Acetic Anhydride2×HCID 764905-Nitropyrimidin-2-amine

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

To 2-amino-5-nitropyrimidine (0.42 g, 3.0 mmol) dissolved in toluene (2 ml) was added acetic anhydride (1.4 ml, 15 mmol). The reaction mixture was stirred at 90° C. for 15 hr, after which an additional amount of acetic anhydride was added (0.7 mL) and the mixture was stirred at reflux for another 16 h. The solvent was removed in vacuo and to the residue was added hexane (10 mL) and DCM (1 mL). The solid was collected by filtration, dried to give N-(5-nitropyrimidin-2-yl)acetamide as an off-white solid. MS (ESI, pos. ion) m/z: 183 (M+1).

Workup

  1. stirringthe mixture was stirred
  2. temperatureat reflux for another 16 h
  3. customThe solvent was removed in vacuo and to the residue
  4. additionwas added hexane (10 mL) and DCM (1 mL)
  5. filtrationThe solid was collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-e0baeb2ebcfd484482e11216a87fde25
Source dataset
uspto-grants-2011_01
Patent number
US07872128B2

Linked notes

Loading…