Ethanol → HCID 15136447, compound

HRID 465970Notes

Reaction equation

HRID 465970 reaction equation
[N:1]1([NH:10][C:11]2[C:16]([N+:17]([O-])=O)=[C:15]([NH:20][N:21]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[CH:23]=[CH:22]3)[N:14]=[CH:13][N:12]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[CH2:30](O)C>C(OCC)(OCC)OCC.C(O)(=O)C>[N:1]1([N:10]2[CH:30]=[N:17][C:16]3[C:11]2=[N:12][CH:13]=[N:14][C:15]=3[NH:20][N:21]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:23]=[CH:22]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

5

Reactant 2

HCID 702EthanolHCID 15136445HCID 15136445, compound

Product 1

HCID 15136447HCID 15136447, compoundYield 252.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 31214Ethyl orthoformateSolvent

Procedure

A mixture of N,N'-bis(1H-indol-1-yl)-5-nitro-4,6-pyrimidinediamine (4 g, 10.4 mmole) in 250 ml ethanol containing 200 mg PtO2 was hydrogenated at 55 psi for four hours, then was filtered and evaporated to 4 g of a solid, m.p. 198°-200° C. A solution of 4-[N-(1H-indol-1-yl)-6-[N-(1H -indol-1-yl)]-4,5,6-pyrimidinetriamine (6 g, 17 mmole) in 25 ml triethyl orthoformate and 9 ml glacial acetic acid stirred one hour at 90° C. then was cooled and evaporated. The residue was dissolved in ether and washed with water, sodium carbonate solution, again with water and saturated sodium chloride, then was dried (anhydrous MgSO4), filtered and evaporated to 6 g of an oil. This oil was purified by flash chromatography to give 4 g of a solid. This solid was recrystallized twice from ethyl acetate-petroleum ether to give 2.8 g (49% overall) of 9-(1H-indol-1-yl)-N-(1H-indol-9H-purin-6-amine, m.p. 196°-198° C.

Workup

  1. filtrationwas filtered
  2. customevaporated to 4 g of a solid, m.p. 198°-200° C
  3. temperaturethen was cooled
  4. customevaporated
  5. dissolutionThe residue was dissolved in ether
  6. washwashed with water, sodium carbonate solution, again with water and saturated sodium chloride
  7. dry with materialwas dried (anhydrous MgSO4)
  8. filtrationfiltered
  9. customevaporated to 6 g of an oil
  10. customThis oil was purified by flash chromatography

Sources & evidence

ORD record
ord-a728da42d2be49ecbdd3bfb9d7a16bb7
Source dataset
uspto-grants-1992_10
Patent number
US05155098

Reaction notes

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