Ethanol → HCID 86749431, compound

HRID 1720757Notes

Reaction equation

HRID 1720757 reaction equation
Cl[C:2]1[C:3]([Cl:9])=[N:4][C:5](Cl)=[N:6][CH:7]=1.[CH3:10][N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.C([OH:19])C>>[CH3:10][N:11]1[CH2:16][CH2:15][N:14]([OH:19])[CH2:13][CH2:12]1.[Cl:9][C:3]1[N:4]=[CH:5][N:6]=[CH:7][CH:2]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 531671-MethylpiperazineHCID 2372592,4,5-Trichloropyrimidine

Product 1

HCID 86749431HCID 86749431, compound

Procedure

Trichloropyrimidine is added in portions to an ice cool solution of N-methylpiperazine (40 g) in ethanol (200 ml). The mixture is then heated at 60° for 2 h. The mixture is concentrated and chromatographed on silica gel with 2-5% methanol and methylene chloride to give 2,4-bis[4-methylpiperazinol-6-chloropyrimidine. This material is heated at 130° in water (30 ml) with piperazine (32 g) in a Parr bomb for 20 h. The product is partitioned between methylene chloride and aqueous sodium carbonate. The phases are separated and the organic phase is dried over sodium sulfate and concentrated to give the title compound, TLC (methylene chloride/methanol/ammonium hydroxide--91.5/8/0.5) Rf =0.3.

Workup

  1. temperatureThe mixture is then heated at 60° for 2 h
  2. concentrationThe mixture is concentrated
  3. customchromatographed on silica gel with 2-5% methanol and methylene chloride

Sources & evidence

ORD record
ord-c8e3115d35974a4e9aaa123c008f1e35
Source dataset
uspto-grants-1996_04
Patent number
US05506354

Reaction notes

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