3-Amino-1-propanol → 9-Ethyl-2-(3-hydroxy-propyl-amino)-6-(3-trifluoromethyl-phenyl-amino)-9H-purine

HRID 9900

Reaction equation

HRID 9900 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]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)[N:3]=1.[NH2:24][CH2:25][CH2:26][CH2:27][OH:28]>C(OCC)(=O)C>[CH2:11]([N:8]1[CH:7]=[N:6][C:5]2[C:9]1=[N:10][C:2]([NH:24][CH2:25][CH2:26][CH2:27][OH:28])=[N:3][C:4]=2[NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=1)[CH3:12]

Participants

4

Reactant 2

HCID 90863-Amino-1-propanolHCID 219881872-chloro-9-ethyl-6-(3-trifluoromethyl-phenyl-amino)-9H-purine

Product 1

HCID 219882069-Ethyl-2-(3-hydroxy-propyl-amino)-6-(3-trifluoromethyl-phenyl-amino)-9H-purine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

200 mg (0.58 mmol) of 2-chloro-9-ethyl-6-(3-trifluoromethyl-phenyl-amino)-9H-purine and 2 ml of 3-amino-1-propanol are stirred at 140° C. for 2 h and the mixture is allowed to cool and is diluted with 60 ml of ethyl acetate. The organic phase is washed with water and dried over sodium sulfate. After removal of the solvent, the residue is recrystallized from ethyl acetate and diethyl ether. 9-Ethyl-2-(3-hydroxy-propyl-amino)-6-(3-trifluoromethyl-phenyl-amino)-9H-purine is obtained; m.p. 136–137° C.; FAB-MS: (M+H)+=381; Rf=0.7 (ethyl acetate:methanol=9:1).

Workup

  1. temperatureto cool
  2. washThe organic phase is washed with water
  3. dry with materialdried over sodium sulfate
  4. customAfter removal of the solvent
  5. customthe residue is recrystallized from ethyl acetate and diethyl ether

Sources & evidence

ORD record
ord-3a5c495ce8bd459ab04cfd5ab755e0c5
Source dataset
uspto-grants-2006_08
Patent number
US07091346B1

Linked notes

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