iMidazo[1,2-a]pyriMidine-6-carboxylic acid

iMidazo[1,2-a]pyriMidine-6-carboxylic acid Property

Density 

1.58±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

-0.43±0.41(Predicted)

Appearance

White to off-white Solid

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

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

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

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.

P321Specific treatment (see … on this label).

P330Rinse mouth.

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

P362Take off contaminated clothing and wash before reuse.

P501Dispose of contents/container to..…

iMidazo[1,2-a]pyriMidine-6-carboxylic acid Chemical Properties,Usage,Production

Synthesis

Step 4. Add methyl imidazo[1,2-A]pyrimidine-6-carboxylate (92 g, 356.5 mmol) and water (200 mL) to a round bottom flask. An aqueous 6N NaOH solution (2.5 eq.) was added slowly and dropwise with stirring at room temperature. The reaction mixture was continued to be stirred at room temperature for 1 hr and then cooled in an ice water bath, followed by the addition of concentrated hydrochloric acid to adjust the pH to 5-6. The reaction solution was concentrated under reduced pressure to about 150 mL (3/4 of the original volume) and cooled again in an ice water bath. The precipitate precipitated was collected by vacuum filtration, washed with cold water (50 mL) and dried to give imidazo[1,2-A]pyrimidine-6-carboxylic acid as an off-white solid (46 g, 79% yield). The product was characterized by 1H NMR (DMSO-d6, 400 MHz): δ 9.29 (d, J = 2.0Hz, 1H), 8.89 (d, J = 2.0Hz, 1H), 7.94 (s, 1H), 7.70 (s, 1H). Mass spectrum (ESI-): m/z 164.1 [M + H]+, 186.1 [M + Na]+.

References

[1] Patent: WO2013/127266, 2013, A1. Location in patent: Page/Page column 130; 131
[2] Patent: WO2013/127267, 2013, A1. Location in patent: Page/Page column 82; 83
[3] Patent: WO2013/127269, 2013, A1. Location in patent: Page/Page column 144
[4] Patent: WO2013/127268, 2013, A1. Location in patent: Page/Page column 60; 61
[5] Patent: WO2013/130935, 2013, A1. Location in patent: Paragraph 0177