Lithium Hydroxide → HCID 57897855, compound

HRID 1693569Notes

Reaction equation

HRID 1693569 reaction equation
C([O:3][C:4](=[O:40])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N:11]2[CH:19]=[N:18][C:17]3[C:16](=[O:20])[N:15]([C:21]4[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=4)[C:14]([C:28]4[CH:33]=[CH:32][C:31]([C:34]5[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=5)=[CH:30][CH:29]=4)=[N:13][C:12]2=3)[CH:6]=1)C.[Li+].[OH-]>C1COCC1.CO.O.O>[C:31]1([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:32]=[CH:33][C:28]([C:14]2[N:15]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)[C:16](=[O:20])[C:17]3[N:18]=[CH:19][N:11]([C:7]4[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=4)[C:4]([OH:40])=[O:3])[C:12]=3[N:13]=2)=[CH:29][CH:30]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 57897854HCID 57897854, compound

Product 1

HCID 57897855HCID 57897855, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A solution of 3-[2-biphenyl-4-yl-1-(4-chloro-phenyl)-6-oxo-1,6-dihydro-purin-9-yl]-benzoic acid ethyl ester (200 mg, 0.37 mmol) in THF/MeOH/H2O 3:2:1 (5 mL) was cooled to 0° C. and treated with 3 N aqueous LiOH (183 μL, 0.55 mmol). The reaction mixture was allowed to warm to room temperature and was stirred for 4 h. The reaction was diluted with H2O, extracted with Et2O, and acidified with 1N aqueous HCl. The resulting white precipitate was collected by suction filtration to provide 3-[2-Biphenyl-4-yl-1-(4-chloro-phenyl)-6-oxo-1,6-dihydro-purin-9-yl]-benzoic acid (155 mg, 82%) as a white solid. HPLC-MS calculated for C30H19ClN4O3 (M+H+): 519.1. Found: 519.1.

Workup

  1. extractionextracted with Et2O
  2. filtrationThe resulting white precipitate was collected by suction filtration

Sources & evidence

ORD record
ord-5aeb0c589b4d44de9828ff3221319871
Source dataset
uspto-grants-2012_04
Patent number
US08158634B2

Reaction notes

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