Hydrochloric Acid → 6-Carbamoylpyrazolo(1,5-a)pyrimidine-3-carboxylic acid

HRID 1773496Notes

Reaction equation

[OH-:1].[Na+].C([O:5][C:6]([C:8]1[CH:9]=[N:10][N:11]2[CH:16]=[C:15]([C:17]#[N:18])[CH:14]=[N:13][C:12]=12)=[O:7])C.Cl>C(O)C>[C:17]([C:15]1[CH:14]=[N:13][C:12]2[N:11]([N:10]=[CH:9][C:8]=2[C:6]([OH:5])=[O:7])[CH:16]=1)(=[O:1])[NH2:18]

Participants

Conditions

Temperature: 60 °C

Procedure

An aqueous solution of sodium hydroxide (10%, 5 mL) was added to a suspension of 6-cyano-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid ethyl ester (0.35 mg, 1.62 mmol) in ethanol (5 mL) and the reaction mixture was heated at 60° C. for 5 hours. Ice-water was added and the resulting mixture was acidified until pH<1 by addition of an aqueous solution of hydrochloric acid (3 M). The solid which crashed out was collected by filtration, washed twice with water, methanol and diethyl ether, dried under reduced pressure to afford 0.25 g (75% yield) of 6-carbamoyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid.

Workup

filtrationThe solid which crashed out was collected by filtration
washwashed twice with water, methanol and diethyl ether
customdried under reduced pressure

Sources & evidence

ORD record: ord-66f84a7d654347be9834591c753e2cb8
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09255110B2

Reaction notes

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