Hydrochloric Acid → HCID 57722608, compound

HRID 1986860Notes

Reaction equation

HRID 1986860 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]2[CH:14]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[CH:12]=[N:11][C:10]=12)=[O:5])C.[OH-].[Na+].Cl>C(O)CCC>[CH3:22][O:21][C:18]1[CH:17]=[CH:16][C:15]([C:13]2[CH:12]=[N:11][C:10]3[N:9]([N:8]=[CH:7][C:6]=3[C:4]([OH:5])=[O:3])[CH:14]=2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57722618HCID 57722618, compound

Product 1

HCID 57722608HCID 57722608, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 6-(4-methoxy-phenyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid ethyl ester (1-1, 660 mg, 2.2 mmol, 1 equiv) and aquoeus sodium hydroxide solution (1N, 11.1 mL, 11.1 mmol, 5.00 equiv) in-BuOH (45 mL) was stirred for 24 hours at 100° C. The yellow solution was poured directly into aqueous 1N HCl solution (500 mL), and the resulting aqueous mixture was extracted with chloroform (3×300 mL). The combined organic layers were dried over sodium sulfate and concentrated to afford 6-(4-methoxy-phenyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (1-2) as a white solid. 1H NMR (400 MHz, DMSO) δ 12.38 (br s, 1H), 9.54 (m, 1H), 9.16 (m, 1H), 8.60 (s, 1H), 7.84 (d, 2H, J=8 Hz), 7.12 (d, 2H, J=8 Hz), 3.85 (s, 3H).

Workup

  1. extractionthe resulting aqueous mixture was extracted with chloroform (3×300 mL)
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-7924f783f1e149619b748be2184d82c8
Source dataset
uspto-grants-2009_06
Patent number
US07550470B2

Reaction notes

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