2,4,6-Trichloropyrimidine → 2,6-Dichloro-N-methylpyrimidin-4-amine

HRID 1441131Notes

Reaction equation

HRID 1441131 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4](Cl)[N:3]=1.Cl.CN.[CH:13]([N:16](C(C)C)CC)(C)C>C1COCC1>[Cl:1][C:2]1[N:3]=[C:4]([NH:16][CH3:13])[CH:5]=[C:6]([Cl:8])[N:7]=1

Participants

5

Reactant 3

HCID 773782,4,6-TrichloropyrimidineHCID 81531DiisopropylethylamineHCID 6364545Methylamine hydrochloride

Product 1

HCID 155636442,6-Dichloro-N-methylpyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2,4,6-Trichloropyrimidine (I, 30 g) is added to a suspension of methylamine hydrochloride (II, 10 g) in THF (250 ml). The mixture is cooled to -6° and diisopropylethylamine (55 ml) is added slowly. The mixture is stirred for 3 days at 20°-25° and then is concentrated under reduced pressure. The residue is absorbed on silica gel (75 g) with ethyl acetate/methylene chloride (1/1) and applied to a silica gel (1 kg) column packed in ethyl acetate/hexane (1/1). Elution is performed with ethyl acetate/hexane (1/1) collecting 500 ml fractions. The appropriate fractions (8-14) are pooled and concentrated to give the title compound, NMR (CDCl3) 6.29, 6.2 and 2.9δ.

Workup

  1. temperatureThe mixture is cooled to -6°
  2. concentrationis concentrated under reduced pressure
  3. customThe residue is absorbed on silica gel (75 g) with ethyl acetate/methylene chloride (1/1)
  4. washElution
  5. customcollecting 500 ml fractions
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7b52316056b34d65a171114fd4afbdbe
Source dataset
uspto-grants-1996_03
Patent number
US05502187

Reaction notes

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