4,6-Dichloro-2-methyl-5-nitropyrimidine → 4,6-Dichloro-2-methylpyrimidin-5-amine

HRID 2121613Notes

Reaction equation

HRID 2121613 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-])=O)=[C:6]([Cl:11])[N:5]=[C:4]([CH3:12])[N:3]=1>C(O)(=O)C.CO.[Fe]>[Cl:1][C:2]1[C:7]([NH2:8])=[C:6]([Cl:11])[N:5]=[C:4]([CH3:12])[N:3]=1

Participants

5

Reactant 1

HCID 831924,6-Dichloro-2-methyl-5-nitropyrimidine

Product 1

HCID 7366744,6-Dichloro-2-methylpyrimidin-5-amine

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

Add iron powder (6.0 g) to a solution of 4,6 dichloro-2-methyl-5-nitro-pyrimidine (6.50 g, 31 mmol) in acetic acid (11 mL) and MeOH (50 mL). Heat the resulting mixture at 65° C. for 1 h. After cooling, to ambient temperature, filter the mixture through a pad of celite, and evaporate the filtrate to dryness under reduced pressure. Treat the residue with 1N aq NaOH, and extract with EtOAc. Wash the EtOAc extract with water and saturated aq NaCl, dry over Na2SO4, filter, and concentrate in vacuo to obtain the title compound as a solid.

Workup

  1. temperatureAfter cooling, to ambient temperature
  2. filtrationfilter the mixture through a pad of celite
  3. customevaporate the filtrate to dryness under reduced pressure
  4. additionTreat the residue with 1N aq NaOH
  5. extractionextract with EtOAc
  6. washWash the EtOAc
  7. extractionextract with water and saturated aq NaCl
  8. dry with materialdry over Na2SO4
  9. filtrationfilter
  10. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-4d603b19c0584eec840bfc0598fd6402
Source dataset
uspto-grants-2004_02
Patent number
US06696445B2

Reaction notes

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