HCID 21504499, compound → HCID 131710506, compound

HRID 1288277Notes

Reaction equation

HRID 1288277 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-])=O)=[CH:5][C:4]=1[C:12]1[N:20]=[C:19]2[C:15](=[N:16][N:17]=[N:18]2)[C:14](=[O:21])[N:13]=1.[H][H]>C(OCCO)C.[Pt]=O>[OH2:2].[NH2:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[C:4]([C:12]2[N:20]=[C:19]3[C:15](=[N:16][N:17]=[N:18]3)[C:14](=[O:21])[N:13]=2)[CH:5]=1.[NH2:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[C:4]([C:12]2[N:20]=[C:19]3[C:15](=[N:16][N:17]=[N:18]3)[C:14](=[O:21])[N:13]=2)[CH:5]=1

Participants

5

Reactant 2

HCID 21504499HCID 21504499, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 131710506HCID 131710506, compoundYield 17.3%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 8076Glycol monoethyl etherSolvent

Procedure

A solution of 2-(2-methoxy-5-nitrophenyl)-8-azapurin-6-one (1.87 g.) (prepared as described in Example 2) in 2-ethoxyethanol (50 ml.) was shaken at room temperature with a platinum oxide catalyst (0.12 g.) under hydrogen (5 kg/cm2). After the uptake of hydrogen was complete, the filtered solution was concentrated to dryness and the brown residual solid was recrystallised from aqueous N,N-dimethylformamide. A portion of this material was further purified by dissolution in 2N ammonium hydroxide solution followed by acidification of the filtered solution with 2N acetic acid. The brown precipitate was filtered, washed well with water and dried to give 2-(5-amino-2-methoxyphenyl)-8-azapurin-6-one hemihydrate (0.2 g.) in the form of a brown solid, m.p. 204°-206° C. (with decomposition, sintering at about 175° C.).

Workup

  1. concentrationthe filtered solution was concentrated to dryness
  2. customthe brown residual solid was recrystallised from aqueous N,N-dimethylformamide
  3. customA portion of this material was further purified by dissolution in 2N ammonium hydroxide solution
  4. filtrationThe brown precipitate was filtered
  5. washwashed well with water
  6. customdried

Sources & evidence

ORD record
ord-19b5e857d4654e8a818a572effc4ae87
Source dataset
uspto-grants-1976_10
Patent number
US03987160

Reaction notes

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