Potassium Hydroxide → HCID 10404737, compound

HRID 2056250Notes

Reaction equation

HRID 2056250 reaction equation
[CH2:1]([C:3]1[N:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[N:9]=[C:8]2[C:4]=1[N:5]=[CH:6][N:7]2[C:16]1[CH:21]=[CH:20][C:19](C(OC)=O)=[CH:18][CH:17]=1)[CH3:2].[OH-:26].[K+].[CH3:28][OH:29].C1COCC1.O>>[C:28]([C:18]1[CH:17]=[C:16]([N:7]2[CH:6]=[N:5][C:4]3[C:8]2=[N:9][C:10]([C:12]([F:15])([F:13])[F:14])=[N:11][C:3]=3[CH2:1][CH3:2])[CH:21]=[CH:20][CH:19]=1)([OH:29])=[O:26]

Participants

4

Reactant 3

HCID 14797Potassium HydroxideHCID 10089213HCID 10089213, compoundHCID 21892291Methanol tetrahydrofuran water

Product 1

HCID 10404737HCID 10404737, compoundYield 22%

Procedure

6-Ethyl-9-(4-methoxycarbonylphenyl)-2-trifluoromethylpurine (500 mg, 1.43 mmol) in 10 mL of MeOH/THF/H2O (1/2/1) was treated with KOH (800 mg, 14.3 mmol) and stirred for 14 hours at room temperature. The reaction mixture was concentrated under vacuum and the residue acidified to pH 4 by the addition of 30% TFA in dichloromethane and extracted with 10% MeOH in dichloromethane. The combined organic extracts were dried (Na2SO4), concentrated under vacuum and crystallized from MeOH to afford 9-(3-carboxyphenyl)-6-ethyl-2-trifluoromethylpurine (110 mg, 22% yield).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. additionthe residue acidified to pH 4 by the addition of 30% TFA in dichloromethane
  3. extractionextracted with 10% MeOH in dichloromethane
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. concentrationconcentrated under vacuum
  6. customcrystallized from MeOH

Sources & evidence

ORD record
ord-2d274adbe0e44487b93f051643abd871
Source dataset
uspto-grants-2008_02
Patent number
US07335654B2

Reaction notes

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