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

HRID 1441132Notes

Reaction equation

HRID 1441132 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4](Cl)[N:3]=1.C(N([CH:16]([CH3:18])[CH3:17])CC)(C)C.Cl.C[NH2:21]>C1COCC1>[Cl:1][C:2]1[N:3]=[C:4]([NH:21][CH2:18][CH2:16][CH3:17])[CH:5]=[C:6]([Cl:8])[N:7]=1

Participants

5

Reactant 3

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

Product 1

HCID 153384322,6-Dichloro-N-propylpyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2,4,6-trichloropyrimidine (I, 11 g) in THF (160 ml) is cooled to -70°. Diisopropylethylamine (11 ml) is added, followed by the addition of a mixture of n-propylamine (II, 4.9 ml) in THY (15 ml). The mixture is allowed to stand for 3 days at 20°-25° and then is concentrated. The residue is partitioned between ethyl acetate and aqueous potassium bicarbonate. The organic extract is washed with water and saline, then dried and concentrated to give a solid. The solid is chromatographed on silica gel (650 g) packed in ethyl acetate/hexane (10/90) and eluted with ethyl acetate/hexane (10→30/90→70). The appropriate fractions (14-18) are pooled and concentrated to give the tire compound, NMR (CDCl3) 6.29, 5.87, 3.21, 1.65 and 0.99δ.

Workup

  1. temperatureis cooled to -70°
  2. concentrationis concentrated
  3. customThe residue is partitioned between ethyl acetate and aqueous potassium bicarbonate
  4. extractionThe organic extract
  5. washis washed with water and saline
  6. customdried
  7. concentrationconcentrated
  8. customto give a solid
  9. customThe solid is chromatographed on silica gel (650 g)
  10. washeluted with ethyl acetate/hexane (10→30/90→70)
  11. concentrationconcentrated
  12. customto give the tire compound, NMR (CDCl3) 6.29, 5.87, 3.21, 1.65 and 0

Sources & evidence

ORD record
ord-0b3a3cbb1694475d8fdcb77c387ecddb
Source dataset
uspto-grants-1996_03
Patent number
US05502187

Reaction notes

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