Triethylamine → HCID 53682266, compound

HRID 893022Notes

Reaction equation

HRID 893022 reaction equation
[CH3:1][C:2]1([CH2:16][N:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[CH2:7][CH2:6][C:5]2[C:8]([CH3:15])=[C:9]([OH:14])[C:10]([CH3:13])=[C:11]([CH3:12])[C:4]=2[O:3]1.[CH2:23]([N:25]([CH2:28][CH3:29])[CH2:26][CH3:27])[CH3:24].Cl[C:31]1C=C(Cl)[N:34]=[CH:33][N:32]=1>C1COCC1.N1CCCC1>[CH3:1][C:2]1([CH2:16][N:17]2[CH2:22][CH2:21][N:20]([C:31]3[CH:24]=[C:23]([N:25]4[CH2:28][CH2:29][CH2:27][CH2:26]4)[N:34]=[CH:33][N:32]=3)[CH2:19][CH2:18]2)[CH2:7][CH2:6][C:5]2[C:8]([CH3:15])=[C:9]([OH:14])[C:10]([CH3:13])=[C:11]([CH3:12])[C:4]=2[O:3]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 709434,6-DichloropyrimidineHCID 10447779HCID 10447779, compound

Product 1

HCID 53682266HCID 53682266, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 31268PyrrolidineSolvent

Procedure

To a stirred suspension of 3,4-dihydro-2,5,7,8-tetramethyl-2-(1-piperazinylmethyl)-2H-1-benzopyran-6-ol (EXAMPLE 126, 0.7 g), triethylamine (0.23 g, 2.3 mmol) and THF (10 ml), cooled to 0° in an ice-water bath, is added in a steady stream 4,6-dichloropyrimidine in THF (5 ml). The cooling bath is removed and the mixture stirred at 20°-25° for 18 hr. Ethyl acetate (50 ml) is added and the mixture is washed with water (50 ml), saline, dried over sodium sulfate and the solvent removed at reduced pressure to leave a residue that is dissolved in pyrrolidine (5 ml). The mixture is heated at reflux for 2 hr and concentrated at reduced pressure. The residue is flashed chromatographed on silica gel (50 g) eluting with ammonia, methanol and ethyl acetate (0.5/4.5/95) to give the product which is crystallized from hexane-ethyl acetate to give the title compound.

Workup

  1. temperaturecooled to 0° in an ice-water bath
  2. customThe cooling bath is removed
  3. additionEthyl acetate (50 ml) is added
  4. washthe mixture is washed with water (50 ml), saline
  5. dry with materialdried over sodium sulfate
  6. customthe solvent removed at reduced pressure
  7. customto leave a residue that
  8. temperatureThe mixture is heated
  9. temperatureat reflux for 2 hr
  10. concentrationconcentrated at reduced pressure
  11. customThe residue is flashed chromatographed on silica gel (50 g)
  12. washeluting with ammonia, methanol and ethyl acetate (0.5/4.5/95)
  13. customto give the product which
  14. customis crystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-cebc99db3d4841a8a293b58e6f596db8
Source dataset
uspto-grants-1992_06
Patent number
US05120843

Reaction notes

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