2,6-DichloropyriMidine-4-carboxaMide

2,6-DichloropyriMidine-4-carboxaMide Property

storage temp. 

Inert atmosphere,Room Temperature

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..…

2,6-DichloropyriMidine-4-carboxaMide Chemical Properties,Usage,Production

Synthesis

The general procedure for the synthesis of 2,6-dichloropyrimidine-4-carboxamides from 2,6-dichloropyrimidine-4-carbonyl chloride is as follows: Scheme 3 Synthesis of 2,6-dichloropyrimidine-4-carboxamide: To a solution of ether (Et2O, 500 mL) containing 2,6-dichloropyrimidine-4-carbonyl chloride (26.13 g, 123.6 mmol), a 0.5 M solution of ammonia dioxane (250 mL, 125 mmol) and diisopropylethylamine (iPr2NEt, 22 mL, 126 mmol), and the titration time was about 50 minutes. The reaction mixture was stirred overnight at room temperature. Subsequently, the reaction solution was concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography with the eluent being a hexane solution of 10-50% ethyl acetate (EtOAc). The fraction containing the target product was collected and the solid residue was obtained after evaporating the solvent under reduced pressure. The solid residue was ground with 10 mL of 10% EtOAc/hexane solution and filtered to afford 2,6-dichloropyrimidine-4-carboxamide as an orange crystalline solid (9.743 g, 50.74 mmol, 41% yield). Product characterization: LC/MS: m/z = 192.2 [M + H]+; 1H NMR (400 MHz, DMSO-d6): δ 8.40 (1H, br s), 8.16 (1H, br s), 8.10 (1H, s).

References

[1] Patent: WO2013/30665, 2013, A1. Location in patent: Page/Page column 105
[2] Patent: WO2014/135955, 2014, A1. Location in patent: Paragraph 0312
[3] Patent: WO2015/31036, 2015, A1. Location in patent: Page/Page column 72; 73
[4] Patent: US2015/175569, 2015, A1. Location in patent: Paragraph 0322
[5] Patent: WO2015/99841, 2015, A1. Location in patent: Page/Page column 62