Triethylamine → 2-Phenyl-5H-indolo[3,2-d]pyrimidine

HRID 2211222Notes

Reaction equation

HRID 2211222 reaction equation
Cl[C:2]1[C:3]2[NH:20][C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:4]=2[N:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:7]=1.C(N(CC)CC)C.[H][H]>[Pd].C(O)C>[C:8]1([C:6]2[N:7]=[CH:2][C:3]3[NH:20][C:19]4[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=4[C:4]=3[N:5]=2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 152847324-Chloro-2-phenyl-5H-indolo[3,2-d]pyrimidineHCID 178418361HCID 178418361, compound

Product 1

HCID 152342772-Phenyl-5H-indolo[3,2-d]pyrimidine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4-Chloro-2-phenyl-5H-indolo[3,2-d]pyrimidine (650 mg), triethylamine (1.0 g), 10% palladium on carbon catalyst (110 mg) and ethanol (30 mL) was stirred under 1 atm of hydrogen for 1 h. The catalyst was filtered through celite and the ethanol is removed in vacuo, the residue is suspended in saturated ammonium chloride solution and the product was extracted with methylene chloride. After drying over magnesium sulfate the solvent was removed in vacuo to afford 2-Phenyl-5H-indolo[3,2-d]pyrimidine (Compound 4) after trituration with ether.

Workup

  1. filtrationThe catalyst was filtered through celite
  2. customthe ethanol is removed in vacuo
  3. extractionthe product was extracted with methylene chloride
  4. dry with materialAfter drying over magnesium sulfate the solvent
  5. customwas removed in vacuo

Sources & evidence

ORD record
ord-b86aaa81762b4055a448e6d0ec7ca312
Source dataset
uspto-grants-1995_10
Patent number
US05463054

Reaction notes

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