Diethylamine → 6-Chloro-N~2~,N~2~,N~4~,N~4~-tetraethylpyrimidine-2,4-diamine

HRID 1109915Notes

Reaction equation

HRID 1109915 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].Cl[C:7]1[C:8]([Cl:14])=[N:9][C:10](Cl)=[N:11][CH:12]=1>C1COCC1.N1C=CC=CC=1>[CH2:1]([N:3]([CH2:4][CH3:5])[C:10]1[N:11]=[C:12]([N:3]([CH2:4][CH3:5])[CH2:1][CH3:2])[CH:7]=[C:8]([Cl:14])[N:9]=1)[CH3:2]

Participants

5

Reactant 2

HCID 8021Diethylamine2×HCID 2372592,4,5-Trichloropyrimidine

Product 1

HCID 176037526-Chloro-N~2~,N~2~,N~4~,N~4~-tetraethylpyrimidine-2,4-diamine

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

Diethylamine (80 g) is reacted with trichloropyrimidine (50 g) in THF. The reaction after chromatography yields a mixture of the mono- and di-adduct. This material is dissolved in pyridine (58 g) and reacted with diethylamine (35 g) at 50° for 3 h. The reaction is concentrated to a residue. The residue is partitioned between methylene chloride and aqueous sodium bicarbonate. The organic phase is separated and concentrated. The residue is chromatographed on silica gel, eluting with ethyl acetate/hexane (10/90). The appropriate fractions are pooled and concentrated to give 2,4-bis[diethylamino]-6-chloropyrimidine. This material is dissolved in pyridine (100 g) and reacted with piperazine (40 g) at 100° for 50 h. Following the above workup procedure the title compound is obtained, NMR (CDCl3) 1.15, 2.90, 3.45 and 4.9 δ.

Workup

  1. customThe reaction after chromatography
  2. customyields
  3. additiona mixture of the mono- and di-adduct
  4. concentrationThe reaction is concentrated to a residue
  5. customThe residue is partitioned between methylene chloride and aqueous sodium bicarbonate
  6. customThe organic phase is separated
  7. concentrationconcentrated
  8. customThe residue is chromatographed on silica gel
  9. washeluting with ethyl acetate/hexane (10/90)
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-549031486e734796b5dce78afd9220c5
Source dataset
uspto-grants-1994_06
Patent number
US05322943

Reaction notes

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