Pyrrolidine → HCID 22418784, compound

HRID 2372629Notes

Reaction equation

HRID 2372629 reaction equation
[CH2:1]([N:3]([CH2:17][CH3:18])[C:4]1[N:9]=[C:8]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[CH:7]=[C:6](Cl)[N:5]=1)[CH3:2].[NH:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1>>[CH2:1]([N:3]([CH2:17][CH3:18])[C:4]1[N:9]=[C:8]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[CH:7]=[C:6]([N:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)[N:5]=1)[CH3:2]

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 22418728HCID 22418728, compound

Product 1

HCID 22418784HCID 22418784, compound

Procedure

A solution of 2-diethylamino-4-piperazino-6-chloro-pyrimidine (4.10 g) in pyrrolidine (4.10 g) is heated for 12 hr at 100°, then concentrated. The concentrate is partitioned between aqueous sodium bicarbonate and methylene chloride. The phases are separated, the organic phase is dried and concentrated to give 2-diethylamino-4-piperazino-6-pyrrolidino-pyrimidine. A solution of this amine (4.01 g). 21-bromo-17α-hydroxypregna-4,9(11)-diene-3,20-dione (5.41 g), and potassium carbonate (1.75 g) are stirred in acetonitrile (200 ml) for 19 hr. The reaction mixture is partitioned between methylene chloride and aqueous sodium bicarbonate. The phases are separated and the organic phase is dried over sodium sulfate and concentrated. The concentrate is chromatographed on silica gel (methylene chloride to 4% methanol/methylene chloride) to give the free base corresponding to the title compound. An ethyl acetate solution of this compound is converted to the hydrochloride salt with ether/hydrochloric acid to give the title compound.

Workup

  1. concentrationconcentrated
  2. customThe concentrate is partitioned between aqueous sodium bicarbonate and methylene chloride
  3. customThe phases are separated
  4. customthe organic phase is dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-de20b1ac5d304668a642d9bdba0b1d3c
Source dataset
uspto-grants-1992_03
Patent number
US05099019

Reaction notes

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