Ethanolamine → 2-[[6-(3-Fluoroanilino)-9-isopropyl-purin-2-yl]amino]ethanol

HRID 9913Notes

Reaction equation

HRID 9913 reaction equation
Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:11]([CH3:13])[CH3:12])=[C:4]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)[N:3]=1.[CH2:22]([CH2:24][NH2:25])[OH:23]>C(OCC)(=O)C>[F:21][C:17]1[CH:16]=[C:15]([NH:14][C:4]2[N:3]=[C:2]([NH:25][CH2:24][CH2:22][OH:23])[N:10]=[C:9]3[C:5]=2[N:6]=[CH:7][N:8]3[CH:11]([CH3:13])[CH3:12])[CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 700EthanolamineHCID 21988324HCID 21988324, compound

Product 1

HCID 98404752-[[6-(3-Fluoroanilino)-9-isopropyl-purin-2-yl]amino]ethanol

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

0.2 g (0.63 mmol) of 2-chloro-9-isopropyl-6-(3-fluoro-phenyl-amino)-9H-purine (prepared according to Stage 91.1) is stirred in 1 ml of ethanolamine at 150° C. for 5 h, and the mixture is then allowed to cool and is diluted with ethyl acetate. The organic phase is washed with water and dried over sodium sulfate. On concentration of the solvent, 6-(3-fluoro-phenyl-amino)-2-(2-hydroxy-ethyl-amino)-9-isopropyl-9H-purine is obtained as a crystalline mass. This is filtered off and dried; m.p. 142° C.; FAB-MS: (M+H)+=330; Rf=0.6 (CH2Cl2:methanol 9:1).

Workup

  1. temperatureto cool
  2. washThe organic phase is washed with water
  3. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-fc726c1fc81845349676ec0b25429a73
Source dataset
uspto-grants-2006_08
Patent number
US07091346B1

Reaction notes

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