2-Amino-4-methyl-5-bromopyrimidine Chemical Properties

Melting point:

192-194℃

Boiling point:

345.4±34.0 °C(Predicted)

Density 

1.699±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

solid

pka

2.47±0.10(Predicted)

Appearance

White to light yellow Solid

InChI

InChI=1S/C5H6BrN3/c1-3-4(6)2-8-5(7)9-3/h2H,1H3,(H2,7,8,9)

InChIKey

LPQVTZJEIXYDQA-UHFFFAOYSA-N

SMILES

C1(N)=NC=C(Br)C(C)=N1

CAS DataBase Reference

17321-93-6

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-37/38-41

Safety Statements 

26-39

WGK Germany 

3

TSCA 

N

HS Code 

29335990

2-Amino-4-methyl-5-bromopyrimidine Usage And Synthesis

Synthesis

General procedure for the synthesis of 2-amino-4-methyl-5-bromopyrimidine from 2-amino-4-methylpyrimidine: To a solution of 4-methylpyrimidin-2-ylamine (10.9 g, 100 mmol) in chloroform (400 mL) was added N-bromosuccinimide (17.8 g, 100 mmol). The reaction mixture was stirred under light-avoiding conditions for 15 hours. Upon completion of the reaction, the mixture was transferred to dichloromethane (140 mL) and washed sequentially with 1N sodium hydroxide solution (3 x 200 mL) and saturated sodium chloride solution (100 mL). The organic phase was dried with anhydrous sodium sulfate, filtered and concentrated to give 5-bromo-4-methylpyrimidin-2-ylamine (18.8 g, 99% yield). The product was detected by LCMS (m/z): 188.0/190.0 (MH+). 1H NMR (CDCl3) data: δ 8.22 (s, 1H), 5.02 (bs, 2H), 2.44 (s, 3H).

References

[1] Patent: WO2007/84786, 2007, A1. Location in patent: Page/Page column 91-92
[2] ACS Medicinal Chemistry Letters, 2011, vol. 2, # 10, p. 774 - 779
[3] Patent: WO2011/130628, 2011, A1. Location in patent: Page/Page column 180
[4] Patent: US2013/102595, 2013, A1. Location in patent: Paragraph 0377; 0378
[5] Patent: JP2015/187145, 2015, A. Location in patent: Paragraph 0330

2-Amino-4-methyl-5-bromopyrimidine(17321-93-6)Related Product Information

• 5-Bromopyrimidine
• 2-Pyrimidinamine, 4-bromo- (9CI)
• 2-Aminopyrimidine
• N,N-Dimethyl-1,4-phenylenediamine
• Pirimiphos-methyl
• 2-Amino-5-bromopyrimidine
• 5-Amino-2-methylpyridine
• METSULFURON METHYL
• Kresoxim-methyl
• Methyl acetate
• Amino tris(methylene phosphonic acid)
• Methyl salicylate
• Methylparaben
• Bensulfuron methyl
• Thiophanate-methyl
• Tris(hydroxymethyl)aminomethane
• Methyl
• Methyl bromide