4,6-Dichloro-2-methyl-5-nitropyrimidine → (6-Chloro-2-methyl-5-nitro-pyrimidin-4-yl)(2,4,6-trimethyl-pyridin-3-yl)amine

HRID 1831716Notes

Reaction equation

HRID 1831716 reaction equation
[CH3:1][C:2]1[N:7]=[C:6](Cl)[C:5]([N+:9]([O-:11])=[O:10])=[C:4]([Cl:12])[N:3]=1.[CH3:13][C:14]1[C:19]([NH2:20])=[C:18]([CH3:21])[CH:17]=[C:16]([CH3:22])[N:15]=1>C(#N)C>[Cl:12][C:4]1[N:3]=[C:2]([CH3:1])[N:7]=[C:6]([NH:20][C:19]2[C:14]([CH3:13])=[N:15][C:16]([CH3:22])=[CH:17][C:18]=2[CH3:21])[C:5]=1[N+:9]([O-:11])=[O:10]

Participants

4

Reactant 2

HCID 831924,6-Dichloro-2-methyl-5-nitropyrimidineHCID 988462,4,6-Trimethyl-3-pyridinamine

Product 1

HCID 10757155(6-Chloro-2-methyl-5-nitro-pyrimidin-4-yl)(2,4,6-trimethyl-pyridin-3-yl)amineYield 36%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2-methyl-5-nitro-4,6-dichloro-pyrimidine (208 mg, 1.00 mmol) in 2.5 ml of acetonitrile was treated with 2,4,6-trimethyl-3-amino-pyridine (273 mg, 2 mmol) stirred at room temperature 2 hours. The mixture was quenched with water and extracted with ethyl acetate. The organic layer was washed with brine, dried and concentrated to give red residue. The residue was purified through silica gel column chromatography using chloroform to 6% methanol in chloroform as eluent to give the title compound (110 mg, 36%) as an orange oil. 1H NMR (CDCl3) 68.78 (brs, 1H), 6.97 (s, 1H), 2.54 (s, 3H), 2.43 (s, 3H), 2.40 (s, 3H), 2.17 (s, 3H) ppm.

Workup

  1. customThe mixture was quenched with water
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customto give red residue
  7. customThe residue was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-87ad2dce7aaa4eb8a1514ad16a92702a
Source dataset
uspto-grants-2006_06
Patent number
US07067664B1

Reaction notes

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