Methylamine → 2-chloro-N-methyl-5-nitropyrimidin-4-amine

HRID 1375387Notes

Reaction equation

HRID 1375387 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.[CH3:12][NH2:13]>O1CCCC1.CC(O)C>[Cl:1][C:2]1[N:7]=[C:6]([NH:13][CH3:12])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 5212662,4-Dichloro-5-nitropyrimidine

Product 1

HCID 71472322-chloro-N-methyl-5-nitropyrimidin-4-amineYield 86.1%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5.82 g (30 mmol) of 2,4-dichloro-5-nitropyrimidine (N. Whittaker, J. Chem. Soc., 1951;1565–1570) in 100 mL of tetrahydrofuran (THF) is cooled to −78° C. and a solution of 4.66 g (60 mmol) of 40% aqueous methylamine in 20 mL of 2-propanol is added dropwise over 5 minutes. After a further 10 minutes at −78° C., the mixture is allowed to warm to room temperature, and the solvent is removed under vacuum. The residue is then extracted into ethyl acetate (EtOAc), washed with water, and dried with sodium sulfate (Na2SO4). Removal of the solvent and chromatography on silica, eluting with hexane/EtOAc (92:8), gives 4.87 g (86%) of the title compound: mp (hexane) 86–87° C. (lit. mp: 90–91° C.; G. B. Barlin, J. Chem. Soc. (B), 1967:954–958).

Workup

  1. customthe solvent is removed under vacuum
  2. extractionThe residue is then extracted into ethyl acetate (EtOAc)
  3. washwashed with water
  4. dry with materialdried with sodium sulfate (Na2SO4)
  5. customRemoval of the solvent and chromatography on silica
  6. washeluting with hexane/EtOAc (92:8)

Sources & evidence

ORD record
ord-751ba0a2f0364308a9ff11bf27e95443
Source dataset
uspto-grants-2007_01
Patent number
US07169778B2

Reaction notes

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