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

HRID 326478Notes

Reaction equation

HRID 326478 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-ba68d0196c5148e99911eb2795abbd68
Source dataset
uspto-grants-1993_12
Patent number
US05268477

Reaction notes

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