Sodium Hydroxide → (S,E)-6-(1-(tert-butoxy)-2-ethoxy-2-oxoethyl)-5-methyl-7-(4-methylpent-1-en-1-yl)pyrazolo[1,5-a]pyrimidine-2-carboxylic acid

HRID 1630325Notes

Reaction equation

HRID 1630325 reaction equation
[C:1]([O:5][C@@H:6]([C:12]1[C:13]([CH3:32])=[N:14][C:15]2[N:16]([N:24]=[C:25]([C:27]([O:29]CC)=[O:28])[CH:26]=2)[C:17]=1/[CH:18]=[CH:19]/[CH2:20][CH:21]([CH3:23])[CH3:22])[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]([CH3:32])=[N:14][C:15]2[N:16]([N:24]=[C:25]([C:27]([OH:29])=[O:28])[CH:26]=2)[C:17]=1/[CH:18]=[CH:19]/[CH2:20][CH:21]([CH3:22])[CH3:23])[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 71267861(S,E)-Ethyl 6-(1-(tert-butoxy)-2-ethoxy-2-oxoethyl)-5-methyl-7-(4-methylpent-1-en-1-yl)pyrazolo[1,5-a]pyrimidine-2-carboxylate

Product 1

HCID 71259118(S,E)-6-(1-(tert-butoxy)-2-ethoxy-2-oxoethyl)-5-methyl-7-(4-methylpent-1-en-1-yl)pyrazolo[1,5-a]pyrimidine-2-carboxylic acidYield 81.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (S,E)-ethyl 6-(1-(tert-butoxy)-2-ethoxy-2-oxoethyl)-5-methyl-7-(4-methylpent-1-en-1-yl)pyrazolo[1,5-a]pyrimidine-2-carboxylate (190 mg, 0.426 mmol) in EtOH (4 mL) was added 1N NaOH (0.426 mL, 0.426 mmol) and the resulting mixture was stirred at room temp for 4 h. At this point LCMS indicated completion of reaction. Solvents were then removed under reduced pressure and the mixture 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,E)-6-(1-(tert-butoxy)-2-ethoxy-2-oxoethyl)-5-methyl-7-(4-methylpent-1-en-1-yl)pyrazolo[1,5-a]pyrimidine-2-carboxylic acid (145 mg, 0.347 mmol, 81% yield) as light yellow solid. 1H NMR (500 MHz, CDCl3) δ 7.20 (s, 1H), 7.01 (d, J=16.1 Hz, 1H), 6.90 (br. s., 1H), 5.57 (s, 1H), 4.48 (d, J=7.3 Hz, 1H), 4.30-4.22 (m, 2H), 2.72 (br. s., 3H), 2.00-1.85 (m, 1H), 1.32-1.25 (m, 3H), 1.18 (s, 9H), 1.10-0.97 (m, 6H). LCMS (M+H)=418.4.

Workup

  1. customcompletion of reaction
  2. customSolvents were then removed under reduced pressure
  3. additionthe mixture 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-0aa86a9068d3420d8af72f3ab17b6278
Source dataset
uspto-grants-2014_07
Patent number
US08791108B2

Reaction notes

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