Sodium → HCID 13321934, compound

HRID 1284886Notes

Reaction equation

HRID 1284886 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][C:5]2[N:6](S(C3C=CC(C)=CC=3)(=O)=O)[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C:13]=2[N:14]=1.[Na].P([O-])(O)(O)=O.[Na+]>C(O)C>[CH3:1][C:2]1[N:3]=[CH:4][C:5]2[NH:6][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C:13]=2[N:14]=1

Participants

5

Reactant 3

HCID 5360545SodiumHCID 13321933HCID 13321933, compoundHCID 23672064Monosodium phosphate

Product 1

HCID 13321934HCID 13321934, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

The residue (2-methyl-5-tosyl-5H-pyrimido-[5,4-b]indole) is taken up in 100 ml of ethanol and combined with a solution of 1.4 g of sodium in 90 ml of ethanol. The mixture is refluxed for 2 hours. Then the mixture is poured into an aqueous sodium dihydrogen phosphate solution. The aqueous phase is extracted by shaking with methylene chloride. The methylene chloride extracts are washed with saturated sodium chloride solution, dried, and evaporated. The residue is chromatographed with a mixture of 10 parts of methylene chloride and one part of methanol on silica gel, thus obtaining 0.13 g of 2-methyl-5H-pyrimido[5,4-b]indole, mp 240°-242° C.

Workup

  1. temperatureThe mixture is refluxed for 2 hours
  2. extractionThe aqueous phase is extracted
  3. washThe methylene chloride extracts are washed with saturated sodium chloride solution
  4. customdried
  5. customevaporated
  6. customThe residue is chromatographed with a mixture of 10 parts of methylene chloride and one part of methanol on silica gel

Sources & evidence

ORD record
ord-d518689a064a44459010636fe0d6bc37
Source dataset
uspto-grants-1986_01
Patent number
US04564610

Reaction notes

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