Acetic Anhydride → 3-(4-Formyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidin-3-yl)propionic acid

HRID 349563Notes

Reaction equation

[C:1](OC(=O)C)(=[O:3])C.[N:8]1[N:12]2[CH2:13][CH2:14][CH2:15][NH:16][C:11]2=[C:10]([CH2:17][CH2:18][C:19]([OH:21])=[O:20])[CH:9]=1>C(O)=O>[CH:1]([N:16]1[CH2:15][CH2:14][CH2:13][N:12]2[N:8]=[CH:9][C:10]([CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[C:11]12)=[O:3]

Participants

Conditions

Temperature: 40 °C

Procedure

To formic acid (50 ml) was added acetic anhydride (60 ml), and the mixture was stirred at 40° C. for 2 hours. The resulting mixture was added to the above oily product [3-(4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidin-3-yl)propionic acid] and the mixture was stirred at room temperature for 15 hours. After evaporation of the solvent in vacuo, to the residue was added water. The mixture was neutralized with saturated aqueous sodium hydrogencarbonate solution, and concentrated in vacuo. The residue was dissolved in methanol, and the insoluble materials were removed by filtration. The filtrate was concentrated in vacuo to give 3-(4-formyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidin-3-yl)propionic acid (23 g) as an oil.

Workup

stirringthe mixture was stirred at room temperature for 15 hours
customAfter evaporation of the solvent in vacuo
additionto the residue was added water
concentrationconcentrated in vacuo
dissolutionThe residue was dissolved in methanol
customthe insoluble materials were removed by filtration
concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-d42debacb9be480f82589e1c0222f641
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07179801B2

Reaction notes

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