2-chloro-N-methyl-5-nitropyrimidin-4-amine → 2-Chloro-N4-methylpyrimidine-4,5-diamine

HRID 524044

Reaction equation

HRID 524044 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH3:9])[C:5]([N+:10]([O-])=O)=[CH:4][N:3]=1>C(O)(=O)C.[Fe]>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH3:9])[C:5]([NH2:10])=[CH:4][N:3]=1

Participants

4

Reactant 1

HCID 71472322-chloro-N-methyl-5-nitropyrimidin-4-amine

Product 1

HCID 71471722-Chloro-N4-methylpyrimidine-4,5-diamineYield 69.4%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 2-chloro-N-methyl-5-nitropyrimidin-4-amine (1.9 g, 10 mmol) in acetic acid (30 mL) was added iron powder (4 g, 71 mmol), and the suspension mixture was heated to 60° C. for 16 hours. The solvent was removed under reduced pressure, and the residue was diluted by brine and ethyl acetate. The solid was filtered off, and the filtrate was extracted with ethyl acetate (50 mL*12). The organic layers were separated, combined, dried over sodium sulfate, filtered and concentrated to give the title compound (1.1 g, 69%). MS (ES+) C5H7ClN4 requires: 159, 161. found: 160, 162 [M+H]+.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionthe residue was diluted by brine and ethyl acetate
  3. filtrationThe solid was filtered off
  4. extractionthe filtrate was extracted with ethyl acetate (50 mL*12)
  5. customThe organic layers were separated
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-56951a43107a4a83be3043c748893928
Source dataset
uspto-grants-2016_05
Patent number
US09340514B2

Linked notes

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