Sodium Hydroxide → HCID 46913377, compound

HRID 925576Notes

Reaction equation

HRID 925576 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][C:28]=1[C:29]([F:32])([F:31])[F:30])[CH2:5][N:6]1[CH:10]=[C:9]([C:11]2[NH:19][C:18]3[C:17](=[O:20])[N:16]([CH2:21][CH2:22][CH3:23])[C:15]([C:24]#N)=[N:14][C:13]=3[N:12]=2)[CH:8]=[N:7]1.[OH-:33].[Na+].C(O)C.[OH2:38]>>[F:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][C:28]=1[C:29]([F:31])([F:30])[F:32])[CH2:5][N:6]1[CH:10]=[C:9]([C:11]2[NH:19][C:18]3[C:17](=[O:20])[N:16]([CH2:21][CH2:22][CH3:23])[C:15]([C:24]([OH:38])=[O:33])=[N:14][C:13]=3[N:12]=2)[CH:8]=[N:7]1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 19096565Water ethanolHCID 46913378HCID 46913378, compound

Product 1

HCID 46913377HCID 46913377, compoundYield 31%

Conditions

Temperature
57.5 °C

Procedure

A mixture of 8-[1-(3-Fluoro-4-trifluoromethyl-benzyl)-1H-pyrazol-4-yl]-6-oxo-1-propyl-6,7-dihydro-1H-purine-2-carbonitrile (65 mg, 0.145 mmol), NaOH (11 mg, 0.290 mmol) and Ethanol:water (3:1) (6 ml) were stirred at 55-60° C. for 2 hours. Reaction mixture was cooled and organic volatiles were evaporated and to the residue water (2 ml) was added and acidified by 2N HCl up to pH (1-2), solid filtered off. The crude product was purified by preparative HPLC to obtain pure 8-[1-(3-Fluoro-4-trifluoromethyl-benzyl)-1H-pyrazol-4-yl]-6-oxo-1-propyl-6,7-dihydro-1H-purine-2-carboxylic acid (21 mg, 31%) as a white solid.

Workup

  1. customReaction mixture
  2. temperaturewas cooled
  3. customorganic volatiles were evaporated and to the residue water (2 ml)
  4. additionwas added
  5. filtrationfiltered off
  6. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-ae73623e8cf142358f5f05f77eb50eb0
Source dataset
uspto-grants-2016_03
Patent number
US09284316B2

Reaction notes

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