Sodium Hydroxide → HCID 86695059, compound

HRID 574326Notes

Reaction equation

HRID 574326 reaction equation
[C:1]([O:5][C@@H:6]([C:11]1[C:12]([CH3:33])=[N:13][C:14]2[N:15]([N:24]=[C:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:26]=2)[C:16]=1[N:17]1[CH2:21][CH2:20][C:19]([CH3:23])([CH3:22])[CH2:18]1)[C:7]([O:9]C)=[O:8])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C(O)C>[C:1]([O:5][C@@H:6]([C:11]1[C:12]([CH3:33])=[N:13][C:14]2[N:15]([N:24]=[C:25]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH:26]=2)[C:16]=1[N:17]1[CH2:21][CH2:20][C:19]([CH3:23])([CH3:22])[CH2:18]1)[C:7]([OH:9])=[O:8])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86695060HCID 86695060, compound

Product 1

HCID 86695059HCID 86695059, compoundYield 36.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(S)-Methyl 2-(tert-butoxy)-2-(7-chloro-5-methyl-2-phenylpyrazolo[1,5-a]pyrimidin-6-yl)acetate (50 mg, 0.13 mmol) was dissolved in DMF (1 mL) and treated with 3,3-dimethylpyrrolidine hydrochloride (17.5 mg, 0.13 mmol) followed by N,N-diisopropylethylamine (0.068 mL, 0.387 mmol). This reaction mixture was stirred at rt for 18 h. The reaction mixture was partitioned between ether and water, and the organic phase was washed with water (2×). The organic phase was dried (MgSO4) and concentrated to give 35 mg of the ester product as a yellow oil. (S)-methyl 2-(tert-butoxy)-2-(7-(3,3-dimethylpyrrolidin-1-yl)-5-methyl-2-phenylpyrazolo[1,5-a]pyrimidin-6-yl)acetate (34 mg, 0.075 mmol) was dissolved in ethanol (1 mL) and treated with 1M NaOH (0.226 mL, 0.226 mmol). The reaction mixture was stirred at rt for 18 h to complete the ester hydrolysis. The crude reaction mixture was partitioned between EtOAc and 1N HCl. The organic phase was dried (Na2SO4) and concentrated. The residue was purified by Biotage (2-10% MeOH/CH2Cl2) to give 12 mg of (S)-2-(tert-butoxy)-2-(7-(3,3-dimethylpyrrolidin-1-yl)-5-methyl-2-phenylpyrazolo[1,5-a]pyrimidin-6-yl)acetic acid as a white solid.

Workup

  1. customThe crude reaction mixture
  2. customwas partitioned between EtOAc and 1N HCl
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified by Biotage (2-10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-673f63558aad4d6c8fef45104d1d6ad0
Source dataset
uspto-grants-2015_05
Patent number
US09034882B2

Reaction notes

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