Hydrochloric Acid → (S)-2-(tert-butoxy)-2-(2-(3-chlorophenyl)-5-methyl-7-(p-tolyl)pyrazolo[1,5-a]pyrimidin-6-yl)acetic acid

HRID 472866Notes

Reaction equation

HRID 472866 reaction equation
[C:1]([O:5][C@@H:6]([C:11]1[C:12]([CH3:34])=[N:13][C:14]2[N:15]([N:24]=[C:25]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[CH:28]=3)[CH:26]=2)[C:16]=1[C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=1)[C:7]([O:9]C)=[O:8])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl>CO>[C:1]([O:5][C@@H:6]([C:11]1[C:12]([CH3:34])=[N:13][C:14]2[N:15]([N:24]=[C:25]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[CH:28]=3)[CH:26]=2)[C:16]=1[C:17]1[CH:18]=[CH:19][C:20]([CH3:23])=[CH:21][CH:22]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66693736(S)-methyl 2-(tert-butoxy)-2-(2-(3-chlorophenyl)-5-methyl-7-(p-tolyl)pyrazolo[1,5-a]pyrimidin-6-yl)acetate

Product 1

HCID 66692959(S)-2-(tert-butoxy)-2-(2-(3-chlorophenyl)-5-methyl-7-(p-tolyl)pyrazolo[1,5-a]pyrimidin-6-yl)acetic acidYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (S)-methyl 2-(tert-butoxy)-2-(2-(3-chlorophenyl)-5-methyl-7-(p-tolyl)pyrazolo[1,5-a]pyrimidin-6-yl)acetate (0.01 g, 0.021 mmol) and 1M NaOH (0.209 ml, 0.209 mmol) in MeOH (3 mL) was heated at reflux for h. Then, cooled, neutralized with 1M HCl (1 mL), concentrated and the residue was taken up in Et2O (25 mL), washed with water (5 mL), brine (5 mL), dried (MgSO4), filtered and concentrated to give (S)-2-(tert-butoxy)-2-(2-(3-chlorophenyl)-5-methyl-7-(p-tolyl)pyrazolo[1,5-a]pyrimidin-6-yl)acetic acid (0.0082 g, 0.017 mmol, 80% yield) as pale yellow solid. 1H NMR (500 MHz, CDCl3) δ: 7.85 (s, 1H), 7.76-7.72 (m, 1H), 7.69 (t, J=6.1 Hz, 2H), 7.42 (dd, J=14.3, 8.2 Hz, 2H), 7.32-7.28 (m, 2H), 6.91 (s, 1H), 5.28 (s, 1H), 2.68 (s, 3H), 2.51 (s, 3H), 1.01 (s, 9H). LCMS (M+H) calcd for C26H22ClN3O3: 464.17. found: 464.3.

Workup

  1. temperatureat reflux for h
  2. temperatureThen, cooled
  3. concentrationconcentrated
  4. washwashed with water (5 mL), brine (5 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-aa77ef242955426d839bf59933138bbe
Source dataset
uspto-grants-2014_01
Patent number
US08633200B2

Reaction notes

Loading…