Sodium Hydroxide → HCID 46913377, compound

HRID 536030Notes

Reaction equation

HRID 536030 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-prop yl-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 upto 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-f74c89ffc2254390ba31400b000ee295
Source dataset
uspto-grants-2014_10
Patent number
US08859566B2

Reaction notes

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