1-Butanol → 2-(6-fluoro-1H-benzo[d]imidazol-1-yl)-9-((R)-8-fluorochroman-4-yl)-6-phenyl-7H-purin-8(9H)-one

HRID 600429Notes

Reaction equation

HRID 600429 reaction equation
Cl[C:2]1[N:10]=[C:9]([N:11]2[C:15]3[CH:16]=[C:17]([F:20])[CH:18]=[CH:19][C:14]=3[N:13]=[CH:12]2)[N:8]=[C:7]2[C:3]=1[NH:4][C:5](=[O:32])[N:6]2[C@H:21]1[C:30]2[C:25](=[C:26]([F:31])[CH:27]=[CH:28][CH:29]=2)[O:24][CH2:23][CH2:22]1.[CH2:33](O)[CH2:34][CH2:35][CH3:36].[C:38](#N)[CH3:39]>>[F:20][C:17]1[CH:18]=[CH:19][C:14]2[N:13]=[CH:12][N:11]([C:9]3[N:8]=[C:7]4[C:3]([NH:4][C:5](=[O:32])[N:6]4[C@H:21]4[C:30]5[C:25](=[C:26]([F:31])[CH:27]=[CH:28][CH:29]=5)[O:24][CH2:23][CH2:22]4)=[C:2]([C:33]4[CH:39]=[CH:38][CH:36]=[CH:35][CH:34]=4)[N:10]=3)[C:15]=2[CH:16]=1

Participants

4

Reactant 3

HCID 2631-ButanolHCID 6342AcetonitrileHCID 576126986-chloro-2-(6-fluoro-1H-benzo[d]imidazol-1-yl)-9-((R)-8-fluorochroman-4-yl)-7H-purin-8(9H)-one

Product 1

HCID 576126842-(6-fluoro-1H-benzo[d]imidazol-1-yl)-9-((R)-8-fluorochroman-4-yl)-6-phenyl-7H-purin-8(9H)-one

Conditions

Temperature
110 °C

Procedure

General procedure for displacement reactions of 6-chloropurinones with aliphatic amines. To 10 mg (0.022 mmol) of 6-chloro-2-(6-fluoro-1H-benzo[d]imidazol-1-yl)-9-((R)-8-fluorochroman-4-yl)-7H-purin-8(9H)-one was added 0.6 mL of 1-butanol, followed by an aliphatic amine (0.1 mL), and the reaction mixture was stirred at 110° C. for 1-2 h (HPLC monitoring). Upon completion of the reaction, the mixture was left to cool to room temperature, was diluted with acetonitrile and filtered through a Nylon 0.45 μm filter. Preparative HPLC purification afforded, after solvent evaporation and drying, the desired product.

Workup

  1. customUpon completion of the reaction
  2. waitthe mixture was left
  3. temperatureto cool to room temperature
  4. filtrationfiltered through a Nylon 0.45 μm
  5. filtrationfilter
  6. customPreparative HPLC purification
  7. customafforded
  8. customafter solvent evaporation
  9. customdrying

Sources & evidence

ORD record
ord-a2cce3db24864e4e8dfe0a72f08362c5
Source dataset
uspto-grants-2011_03
Patent number
US07902187B2

Reaction notes

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