Ethanolamine → 2-[9-Ethyl-6-(3-fluoro-phenylamino)-9H-purin-2-ylamino]-ethanol

HRID 9912Notes

Reaction equation

HRID 9912 reaction equation
Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][CH3:12])=[C:4]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=2)[N:3]=1.[CH2:21]([CH2:23][NH2:24])[OH:22]>C(OCC)(=O)C>[OH:22][CH2:21][CH2:23][NH:24][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][CH3:12])=[C:4]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=2)[N:3]=1

Participants

4

Reactant 2

HCID 700EthanolamineHCID 219883192-chloro-9-ethyl-6-(3-fluoro-phenyl-amino)-9H-purine

Product 1

HCID 219882472-[9-Ethyl-6-(3-fluoro-phenylamino)-9H-purin-2-ylamino]-ethanol

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

0.2 g (0.62 mmol) of 2-chloro-9-ethyl-6-(3-fluoro-phenyl-amino)-9H-purine (prepared according to Stage 90.2) is stirred in 1 ml of ethanolamine at 150° C. for 3 h, and the mixture is allowed to cool and is diluted with ethyl acetate. The organic phase is washed with water, separated off and dried over sodium sulfate. On concentration, 2-(2-hydroxy-ethyl-amino)-6-(3-fluoro-phenyl-amino)-9-ethyl-9H-purine is obtained as a crystalline precipitate. This precipitate is filtered off and dried; m.p. 184° C.; FAB-MS: (M+H)+=317; Rf=0.5 (CH2Cl2:methanol=9:1).

Workup

  1. temperatureto cool
  2. washThe organic phase is washed with water
  3. customseparated off
  4. dry with materialdried over sodium sulfate
  5. concentrationOn concentration

Sources & evidence

ORD record
ord-65634670e10c47c68865d9e95be13558
Source dataset
uspto-grants-2006_08
Patent number
US07091346B1

Reaction notes

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