Hydrochloric Acid → 5-pyrrolidin-1-yl-7-(tetrahydro-2H-pyran-4-ylamino)pyrazolo[1,5-a]pyrimidine-2-carboxylic acid

HRID 869715Notes

Reaction equation

HRID 869715 reaction equation
[N:1]1([C:6]2[CH:11]=[C:10]([NH:12][CH:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)[N:9]3[N:19]=[C:20]([C:22]([O:24]CC)=[O:23])[CH:21]=[C:8]3[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].Cl>C(O)C.O1CCCC1>[N:1]1([C:6]2[CH:11]=[C:10]([NH:12][CH:13]3[CH2:14][CH2:15][O:16][CH2:17][CH2:18]3)[N:9]3[N:19]=[C:20]([C:22]([OH:24])=[O:23])[CH:21]=[C:8]3[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67408425ethyl 5-pyrrolidin-1-yl-7-(tetrahydro-2H-pyran-4-ylamino)pyrazolo[1,5-a]pyrimidine-2-carboxylate

Product 1

HCID 674075435-pyrrolidin-1-yl-7-(tetrahydro-2H-pyran-4-ylamino)pyrazolo[1,5-a]pyrimidine-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 5-pyrrolidin-1-yl-7-(tetrahydro-2H-pyran-4-ylamino)pyrazolo[1,5-a]pyrimidine-2-carboxylate (1.89 g, 5.26 mmol) in ethanol (25 mL) and tetrahydrofuran (25 mL) was added 1N aqueous sodium hydroxide (10.5 mL, 10.5 mmol) at room temperature. After being stirred for 23 h at same temperature, 6N aqueous hydrochloric acid (1.75 mL, 3.50 mmol), and then the reaction mixture was concentrated in vacuo. The residue was triturated with diisopropyl ether to give 5-pyrrolidin-1-yl-7-(tetrahydro-2H-pyran-4-ylamino)pyrazolo[1,5-a]pyrimidine-2-carboxylic acid. MS (APCI): m/z 330 (M−H).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customThe residue was triturated with diisopropyl ether

Sources & evidence

ORD record
ord-457c0f508ec24934902457d327a44883
Source dataset
uspto-grants-2015_03
Patent number
US08969376B2

Reaction notes

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