Potassium Carbonate → HCID 22418808, compound

HRID 326482Notes

Reaction equation

HRID 326482 reaction equation
[N:1]1([C:6]2[N:11]=[C:10]([N:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)[CH:9]=[C:8]([N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].S([O-])(=O)(=O)C>C(#N)C>[N:1]1([C:6]2[N:11]=[C:10]([N:12]3[CH2:17][CH2:16][N:15]([CH2:9][CH2:10][N:12]4[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]4)[CH2:14][CH2:13]3)[CH:9]=[C:8]([N:18]3[CH2:19][CH2:20][CH2:21][CH2:22]3)[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 85257MethanesulfonateHCID 145852434-(Piperazin-1-yl)-2,6-di(pyrrolidin-1-yl)pyrimidine

Product 1

HCID 22418808HCID 22418808, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The N-protected 2-hydroxyethylpiperazine (3.0 g), triethylamine (1.42 g) and methylene chloride (30 ml) is cooled to 0° in an ice bath under nitrogen. A mixture of methanesulfonyl chloride (1.64 g) in methylene chloride (30 ml) is added dropwise over 10 min. The cooling bath is removed and the mixture allowed to warm to 20°-25° for 30 min. The mixture is then washed with water (60 ml), dried over sodium sulfate and the solvent removed to give crude mesylate. 4-[2,6-Bis(1-pyrrolidinyl)-4-pyrimidinyl]piperazine (4.23 g), potassium carbonate (1.93 g) and acetonitrile (150 ml) are added to the crude mesylate. The mixture is heated at reflux for 18 hr. The acetonitrile is removed under reduced pressure and the residue distributed between chloroform (200 ml) and water (200 ml). The phases are separated, the organic phase is washed with saline, dried over sodium sulfate and the solvent removed under reduced pressure to give an oil. The oil is flash chromatographed on silica gel (200 g) with ethyl acetate/methanol/ammonium hydroxide (9.5/0.4/0.1). The appropriate fractions are pooled and concentrated to give the N-protected form of the title compound as a solid, mp 148°-149°.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 18 hr
  3. customThe acetonitrile is removed under reduced pressure
  4. customThe phases are separated
  5. washthe organic phase is washed with saline
  6. dry with materialdried over sodium sulfate
  7. customthe solvent removed under reduced pressure
  8. customto give an oil
  9. customchromatographed on silica gel (200 g) with ethyl acetate/methanol/ammonium hydroxide (9.5/0.4/0.1)
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-0768d95a338445199a758422a11c9f1b
Source dataset
uspto-grants-1993_12
Patent number
US05268477

Reaction notes

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