6-chloro-N-methyl-pyrimidine-4,5-diamine

6-chloro-N-methyl-pyrimidine-4,5-diamine Property

Melting point:

62℃

Density 

1.447

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

Appearance

Off-white to light yellow Solid

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H302Harmful if swallowed

H312Harmful in contact with skin

H315Causes skin irritation

H318Causes serious eye damage

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

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

P271Use only outdoors or in a well-ventilated area.

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.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

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

P310Immediately call a POISON CENTER or doctor/physician.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P321Specific treatment (see … on this label).

P322Specific measures (see …on this label).

P330Rinse mouth.

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

P362Take off contaminated clothing and wash before reuse.

P363Wash contaminated clothing before reuse.

P501Dispose of contents/container to..…

6-chloro-N-methyl-pyrimidine-4,5-diamine Chemical Properties,Usage,Production

Synthesis

General procedure for the synthesis of 6-chloro-4-methylpyrimidine-4,5-diamine from 4,6-dichloro-5-amino-pyrimidine and monomethylamine: a mixture of 5-amino-4,6-dichloropyrimidine (5,1.0 mmol), triethylamine (1.0 mmol), ethanol (4.3 mL), and monomethylamine (2.5 mmol) was placed in a steel cylinder and reacted for 3 hours by heating to 55°C. After completion of the reaction, the volatiles were removed under reduced pressure. The crude product was purified by silica gel column chromatography with the eluent CHCl3-cC6H12-CH3OH (70:20:10), followed by recrystallization with EtOAc to afford the target compound, 6-chloro-4-methylpyrimidine-4,5-diamine (6), as a white solid (148 mg, 93% yield). The product characterization data were as follows: melting point 165-67 °C; 1H NMR (400 MHz, [D6]DMSO) δ 2.89 (d, J=4.4 Hz, 3H, CH3), 4.96 (br s, 2H, NH2), 6.86 (br q, J=4.4 Hz, 1H, NH), 7.75 (s, 1H, H-2); elemental analysis ( C5H7ClN4) is consistent with theoretical values.

References

[1] European Journal of Medicinal Chemistry, 2018, vol. 151, p. 199 - 213
[2] Patent: US2009/5359, 2009, A1. Location in patent: Page/Page column 21
[3] Patent: US2010/298267, 2010, A1. Location in patent: Page/Page column 15
[4] Journal of Applied Chemistry, 1954, vol. 4, p. 72,74
[5] Collection of Czechoslovak Chemical Communications, 2011, vol. 76, # 11, p. 1379 - 1393