Piperazine → HCID 3023263, compound

HRID 1109926Notes

Reaction equation

HRID 1109926 reaction equation
Cl[C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[NH:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1>>[N:3]1[CH:4]=[CH:5][CH:6]=[N:7][C:2]=1[CH:9]1[CH2:10][NH:11][CH2:12][CH2:13][NH:8]1

Participants

3

Reactant 2

HCID 4837PiperazineHCID 744042-Chloropyrimidine

Product 1

HCID 3023263HCID 3023263, compound

Procedure

A mixture of 2-chloropyrimidine (10.0 g) and piperazine (16 g) in alcohol (120 ml) is stirred for 21 hr. The mixture is partitioned between methylene chloride and aqueous sodium bicarbonate, the phases are separated and the organic phase is dried with sodium sulfate and concentrated to give 2-pyrimidinyl piperazine. The 2-pyrimidinyl piperazine (4.64 g) is stirred at 70° in acetonitrile (200 ml) with 21-bromo-17α-hydroxypregna-4,9(11)-diene-3,20-dione (11.52 g) and potassium carbonate (3.75 g) for 1.5 hr and at 20°-25° for 2 days. The mixture is partitioned between methylene chloride and aqueous sodium bicarbonate, the phases are separated and the organic phase is dried with sodium sulfate and concentrated. The concentrate is chromatographed on silica gel eluting with 4 to 6% methanol/methylene chloride. The appropriate fractions are pooled and concentrated to give the title compound which is crystallized from ethyl acetate.

Workup

  1. customThe mixture is partitioned between methylene chloride and aqueous sodium bicarbonate
  2. customthe phases are separated
  3. dry with materialthe organic phase is dried with sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1962f68e35d24e49baddd19bfc40a84d
Source dataset
uspto-grants-1994_06
Patent number
US05322943

Reaction notes

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