2-Pyrimidinamine, 5-fluoro- (9CI) Chemical Properties

Melting point:

192-193℃

Boiling point:

280℃

Density 

1.372

Flash point:

123℃

storage temp. 

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

form 

powder

pka

2.13±0.10(Predicted)

color 

Off white

InChI

InChI=1S/C4H4FN3/c5-3-1-7-4(6)8-2-3/h1-2H,(H2,6,7,8)

InChIKey

FUNBZJKZJGKXQB-UHFFFAOYSA-N

SMILES

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

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36

Safety Statements 

26

HS Code 

2933599590

2-Pyrimidinamine, 5-fluoro- (9CI) Usage And Synthesis

Uses

2-Amino-5-fluoropyrimidine can be used as a synthetic intermediate in pharmaceuticals and chemicals.

Synthesis

General Steps: Pre-step A Synthesis of 5-fluoro-2-pyrimidinamine A mixed solution of 2-chloro-5-fluoropyrimidine (280 μL, 2.264 mmol) and ammonia (5 mL, 68 mmol) in methanol (860 μL) was placed in a microwave reactor and heated to 110 °C for 30 min of reaction. After completion of the reaction, the reaction mixture was filtered and the resulting solid was washed with methanol. After drying, 5-fluoro-2-pyrimidinamine (247 mg, 2.184 mmol, 96% yield) was obtained as a white crystalline solid. Mass spectrum (electrospray positive ion mode) m/z 114.0 ([M+H]+). Mass spectrum (electrospray positive ionization mode) m/z 409.4 ([M+H]+) of 5-fluoro-2-pyrimidinamine (83 mg, 0.738 mmol). 1H NMR (400 MHz, methanol-d4) δ ppm 1.06-1.23 (m, 2H), 1.32-1.43 (m, 1H), 1.51-1.66 (m, 4H), 1.73-1.94 (m, 4H), 2.15-2.29 (m, 1H), 2.48-2.63 (m, 1H), 2.85-2.99 (m , 1H), 3.20-3.29 (m, 1H), 3.49 (dd, J = 14.02, 4.42 Hz, 1H), 3.69-3.84 (m, 1H), 3.94 (tt, J = 9.57, 4.83 Hz, 1H), 4.76 (dd, J = 6.82, 2.53 Hz, 1H), 7.85 (s, 0.7H), and 8.25 (s, 0.3H), 8.58 (s, 2H).

References

[1] Patent: US2013/345120, 2013, A1. Location in patent: Page/Page column
[2] Patent: US8901119, 2014, B2. Location in patent: Page/Page column
[3] Patent: US9617268, 2017, B2. Location in patent: Page/Page column 372

2-Pyrimidinamine, 5-fluoro- (9CI)(1683-85-8)Related Product Information

• Sulfoxaflor
• triflumezopyrim
• 4-Amino-2,6-dimethoxypyrimidine
• 2,4,6-Triaminopyrimidine
• 5-Fluoropyrimidine