Triethylamine → HCID 68742816, compound

HRID 1714766Notes

Reaction equation

HRID 1714766 reaction equation
[CH3:1][C:2]1[C:10]2[C:9](=[O:11])[NH:8][C:7]([S:12][CH2:13][CH2:14][CH2:15][N:16]3[CH2:21][CH2:20][N:19]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=4)[CH2:18][CH2:17]3)=[N:6][C:5]=2[S:4][C:3]=1C(O)=O.C([N:33](CC)CC)C.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1>C(O)(C)(C)C>[NH2:33][C:3]1[S:4][C:5]2[N:6]=[C:7]([S:12][CH2:13][CH2:14][CH2:15][N:16]3[CH2:17][CH2:18][N:19]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=4)[CH2:20][CH2:21]3)[NH:8][C:9](=[O:11])[C:10]=2[C:2]=1[CH3:1]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 23155671HCID 23155671, compound

Product 1

HCID 68742816HCID 68742816, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

In 20 ml of tert-butanol, 470 Milligrams of 5-methyl-4-oxo-2-[3-(4-pyridin-2-ylpiperazin-1-yl)propylthio]-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylic acid as synthesized in Example 2-17 was dissolved to which 107 mg of triethylamine and 305 mg of DPPA were added by the order stated, followed by 9 hours' heating under reflux. Distilling the solvent off under reduced pressure, the residue was purified on silica gel column chromatography (chloroform:methanol=50:1). The purified product was added to 6 ml of 4N-hydrochloric acid-dioxane solution, stirred for an overnight and from which the solvent was distilled off under reduced pressure. To the residue chloroform was added, followed by washing with saturated aqueous sodium hydrogencarbonate solution, drying over anhydrous magnesium sulfate and removal of the solvent by distillation under reduced pressure. The residue was purified on silica gel column chromatography (chloroform:methanol=25:1) to provide 78 mg (18%) of 6-amino-5-methyl-2-[3-(4-pyridin-2-ylpiperazin-1-yl)propylthio]-3H-thieno[2,3-d]pyrimidin-4-one.

Workup

  1. additionwere added by the order
  2. temperature' heating
  3. temperatureunder reflux
  4. distillationDistilling the solvent off under reduced pressure
  5. customthe residue was purified on silica gel column chromatography (chloroform:methanol=50:1)
  6. additionThe purified product was added to 6 ml of 4N-hydrochloric acid-dioxane solution
  7. distillationwas distilled off under reduced pressure
  8. additionTo the residue chloroform was added
  9. washby washing with saturated aqueous sodium hydrogencarbonate solution
  10. dry with materialdrying over anhydrous magnesium sulfate and removal of the solvent by distillation under reduced pressure
  11. customThe residue was purified on silica gel column chromatography (chloroform:methanol=25:1)

Sources & evidence

ORD record
ord-bcd9b6c8babe4061ad281ccced574d66
Source dataset
uspto-grants-2010_09
Patent number
US07799775B2

Reaction notes

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