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

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

Density 

1.43

refractive index 

1.677

storage temp. 

2-8°C

Appearance

White to off-white Solid

Safety

Hazard Codes 

Xi,Xn

Risk Statements 

22

HazardClass 

IRRITANT

HS Code 

2933998090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

5,7-DIMETHYL-PYRAZOLO[1,5-A]PYRIMIDINE-3-CARBOXYLIC ACID Chemical Properties,Usage,Production

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

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