Water → 5-Oxo-4,5-dihydro-pyrazolo[1,5-a]pyriMidine-3-carboxylic acid

HRID 474320Notes

Reaction equation

HRID 474320 reaction equation
[O:1]=[C:2]1[N:7]=[CH:6][N:5]2[N:8]=[CH:9][C:10]([C:11]([O:13]C)=[O:12])=[C:4]2[CH2:3]1.[OH-].[Li+].O>C(O)(=O)C>[O:1]=[C:2]1[CH:3]=[CH:4][N:5]2[N:8]=[CH:9][C:10]([C:11]([OH:13])=[O:12])=[C:6]2[NH:7]1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 66677507HCID 66677507, compound

Product 1

HCID 1357417735-Oxo-4,5-dihydro-pyrazolo[1,5-a]pyriMidine-3-carboxylic acidYield 93.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of methyl 5-oxo-4,5-dihydropyrazolo[1,5-c]pyrimidine-3-carboxylate (0.75 g 3.89 mM, 1.0 equiv), lithium hydroxide (0.466 g, 19.4 mM, 5.0 equiv) and 20 mL of water was stirred at ambient temperature for 3 hours. HPLC indicated complete reaction. Acetic acid (5 mL) was added and the precipitated solid was collected by vacuum filtration to give 0.65 g (93%) 5-oxo-4,5-dihydropyrazolo[1,5-a]pyrimidine-3-carboxylic acid. 1H NMR (400 MHz, DMSO-d6) δ: 12.5 (br s, 1H,), 11.3 (br s, 1H), 8.57 (d, 1H), 8.08 (d, 1H), 6.15 (d, 1H).

Workup

  1. customreaction
  2. filtrationthe precipitated solid was collected by vacuum filtration

Sources & evidence

ORD record
ord-8058addddebc4a929724e2ea74e63e71
Source dataset
uspto-grants-2014_01
Patent number
US08637526B2

Reaction notes

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