Tetrahydrofuran → HCID 178524809, compound

HRID 1426963Notes

Reaction equation

HRID 1426963 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[CH:9][C:10]([C:11]([O:13]CC)=[O:12])=[C:4]2[N:3]=1.C1COCC1.O.[OH-].[Li+]>CO>[OH:1][C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[CH:9][C:10]([C:11]([OH:13])=[O:12])=[C:4]2[N:3]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 178469952HCID 178469952, compound

Product 1

HCID 178524809HCID 178524809, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 5-hydroxypyrazolo[1,5-a]pyrimidine-3-carboxylate (Preparation B, Step A; 2.0 g, 9.65 mmol) in a 2:1 mixture of THF:MeOH, (40 mL) was added lithium hydroxide monohydrate (29 mL, 29.0 mmol, 1.0 M in water). The solution was stirred at reflux for 16 hours then cooled and concentrated. The residue was dissolved in water (100 mL) and acidified with 6M HCl. The resulting white precipitate was collected by filtration and washed with water and Et2O, then dried under reduced pressure to afford 5-hydroxypyrazolo[1,5-a]pyrimidine-3-carboxylic acid (1.18 g, 68% yield) as a white solid. 1H NMR (d6-DMSO) δ 8.50 (d, 2H, J=7.7 Hz), 8.02 (s, 2H), 6.07 (d, 2H, J=8.2 Hz)

Workup

  1. temperatureat reflux for 16 hours
  2. temperaturethen cooled
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in water (100 mL)
  5. filtrationThe resulting white precipitate was collected by filtration
  6. washwashed with water and Et2O
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-32ddf49102b84ad09aba3c0b8d3e3f43
Source dataset
uspto-grants-2015_01
Patent number
US08933084B2

Reaction notes

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