Sodium Hydroxide → (S)-6-(1-(tert-butoxy)-2-ethoxy-2-oxoethyl)-7-(4,4-dimethylpiperidin-1-yl)-5-methylpyrazolo[1,5-a]pyrimidine-2-carboxylic acid

HRID 1630329Notes

Reaction equation

HRID 1630329 reaction equation
[C:1]([O:5][C@@H:6]([C:12]1[C:13]([CH3:34])=[N:14][C:15]2[N:16]([N:26]=[C:27]([C:29]([O:31]CC)=[O:30])[CH:28]=2)[C:17]=1[N:18]1[CH2:23][CH2:22][C:21]([CH3:25])([CH3:24])[CH2:20][CH2:19]1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CCO>[C:1]([O:5][C@@H:6]([C:12]1[C:13]([CH3:34])=[N:14][C:15]2[N:16]([N:26]=[C:27]([C:29]([OH:31])=[O:30])[CH:28]=2)[C:17]=1[N:18]1[CH2:23][CH2:22][C:21]([CH3:25])([CH3:24])[CH2:20][CH2:19]1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 71267856(S)-ethyl 6-(1-(tert-butoxy)-2-ethoxy-2-oxoethyl)-7-(4,4-dimethylpiperidin-1-yl)-5-methylpyrazolo[1,5-a]pyrimidine-2-carboxylate

Product 1

HCID 71259137(S)-6-(1-(tert-butoxy)-2-ethoxy-2-oxoethyl)-7-(4,4-dimethylpiperidin-1-yl)-5-methylpyrazolo[1,5-a]pyrimidine-2-carboxylic acidYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (S)-ethyl 6-(1-(tert-butoxy)-2-ethoxy-2-oxoethyl)-7-(4,4-dimethylpiperidin-1-yl)-5-methylpyrazolo[1,5-a]pyrimidine-2-carboxylate (220 mg, 0.464 mmol) in EtOH (5 mL) was added 1N NaOH (0.464 mL, 0.464 mmol) and the resulting mixture was stirred at room temp for 4 h. A this point LCMS indicated completion of reaction. Solvents were then removed under reduced pressure and the residue was diluted with water (3 mL), acidified with 1N HCl, extracted with ethyl acetate (25 mL), washed with brine (10 mL), dried (Na2SO4), filtered and concentrated to afford (S)-6-(1-(tert-butoxy)-2-ethoxy-2-oxoethyl)-7-(4,4-dimethylpiperidin-1-yl)-5-methylpyrazolo[1,5-a]pyrimidine-2-carboxylic acid (180 mg, 0.403 mmol, 87% yield) as light yellow solid. 1H NMR (400 MHz, CDCl3) δ 7.14 (s, 1H), 5.95 (s, 1H), 4.31-4.16 (m, 2H), 2.66 (s, 3H), 1.82-1.60 (m, 4H), 1.60-1.46 (m, 4H), 1.28-1.22 (m, 12H), 1.14 (s, 6H). LCMS (M+H)=447.4.

Workup

  1. customcompletion of reaction
  2. customSolvents were then removed under reduced pressure
  3. additionthe residue was diluted with water (3 mL)
  4. extractionextracted with ethyl acetate (25 mL)
  5. washwashed with brine (10 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-654b66cf80e04b66902393e2b6562dec
Source dataset
uspto-grants-2014_07
Patent number
US08791108B2

Reaction notes

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