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90349-23-8

90349-23-8 Structure

90349-23-8 Structure
IdentificationBack Directory
[Name]

5,7-DIMETHYL-PYRAZOLO[1,5-A]PYRIMIDINE-3-CARBOXYLIC ACID
[CAS]

90349-23-8
[Synonyms]

133800
SBB006994
5677-29-2
ALINDA 7268
AKOS B001272
BAS 16984927
MLS000715307
SMR000275286
AKOS BBS-00002689
VITAS-BB TBB005266
TIMTEC-BB SBB006994
ART-CHEM-BB B001272
5,7-dimethyl-3-pyrazolo[1,5-a]pyrimidinecarboxylic acid
5,7-DIMETHYLPYRAZOLO[5,4-A]PYRIMIDINE-3-CARBOXYLIC ACID
5,7-DIMETHYL-PYRAZOLO[1,5-A]PYRIMIDINE-3-CARBOXYLIC ACID
pyrazolo[1,5-a]pyrimidine-3-carboxylic acid, 5,7-dimethyl-
5,7-dimethylpyrazolo[1,5-a]pyrimidine-3-carboxylic acid(SALTDATA: FREE)
[Molecular Formula]

C9H9N3O2
[MDL Number]

MFCD01051014
[MOL File]

90349-23-8.mol
[Molecular Weight]

191.19
Chemical PropertiesBack Directory
[density ]

1.43
[refractive index ]

1.677
[storage temp. ]

2-8°C
[Appearance]

White to off-white Solid
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H315-H319
[Precautionary statements ]

P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313
[Hazard Codes ]

Xi,Xn
[Risk Statements ]

22
[HazardClass ]

IRRITANT
[HS Code ]

2933998090
Hazard InformationBack Directory
[Uses]

5,7-Dimethylpyrazolo[1,5-a]pyrimidine-3-carboxylic Acid is used as a reactant in the synthetic preparation of noninhibitory small molecule chaperones of glucocerebrosidase.
[Synthesis]

ethyl 5,7-dimethylpyrazolo[1,5-a]pyrimidine-3-carboxylate

52664-01-4

5,7-DIMETHYL-PYRAZOLO[1,5-A]PYRIMIDINE-3-CARBOXYLIC ACID

90349-23-8

General procedure for the synthesis of 5,7-dimethylpyrazolo[1,5-a]pyrimidine-3-carboxylic acid from ethyl 5,7-dimethylpyrazolo[1,5-a]pyrimidine-3-carboxylate: to a solution of 5,7-dimethylpyrazolo[1,5-a]pyrimidine-3-carboxylic acid ethyl 5,7-dimethylpyrazolo[1,5-a]pyrimidine-3-carboxylate (2.2g, 10.0mmol) in methanol (15mL), was added an aqueous sodium hydroxide solution (5.67 mL, 7.2 M) and the reaction mixture was heated to reflux at 80 °C for 5 hours. After the reaction was completed, it was cooled to room temperature and neutralized with 2M hydrochloric acid. After neutralization, a white solid precipitated from the solution, which was collected by filtration, washed sequentially with water and ether, and dried in vacuum to afford 5,7-dimethylpyrazolo[1,5-a]pyrimidine-3-carboxylic acid as a white solid (1.3 g, 68% yield). The product was characterized by 1H NMR (400 MHz, DMSO-d6): δ 8.21 (s, 1H), 6.84 (s, 1H), 2.65 (s, 3H), 2.53 (s, 3H). Electrospray mass spectrometry (ES-MS) showed m/z 192.00 ([M+H]+).

[References]

[1] Monatshefte fur Chemie, 2016, vol. 147, # 12, p. 2221 - 2234
[2] Patent: WO2016/73895, 2016, A1. Location in patent: Paragraph 00220
[3] Patent: WO2012/78855, 2012, A1. Location in patent: Page/Page column 17
[4] Journal of Medicinal Chemistry, 2012, vol. 55, # 12, p. 5734 - 5748
[5] Journal of Heterocyclic Chemistry, 2018, vol. 55, # 1, p. 214 - 225
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