2-DIMETHYLAMINO-PYRIMIDINE-5-CARBALDEHYDE Chemical Properties

Melting point:

122-124 °C

Boiling point:

289.6±32.0 °C(Predicted)

Density 

1.204±0.06 g/cm3(Predicted)

storage temp. 

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

form 

solid

pka

2.27±0.10(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C7H9N3O/c1-10(2)7-8-3-6(5-11)4-9-7/h3-5H,1-2H3

InChIKey

XBYXYDVSCMMJDT-UHFFFAOYSA-N

SMILES

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

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22-43

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2933599590

2-DIMETHYLAMINO-PYRIMIDINE-5-CARBALDEHYDE Usage And Synthesis

Synthesis

General procedure for the synthesis of 2-dimethylaminopyrimidine-5-carbaldehyde from 2-chloropyrimidine-5-carbaldehyde: 2-chloropyrimidine-5-carbaldehyde (412 mg, 2.89 mmol) and triethylamine (Et3N, 482 μL, 3.47 mmol) were dissolved in dioxane (20 mL), followed by the addition of a solution of dimethylamine (Me2NH) in tetrahydrofuran (THF) (1.59 mL, 2.0 M, 3.18 mmol). The reaction mixture was stirred at room temperature for 1 h. After completion of the reaction, the reaction solution was filtered and the solid was washed with dioxane (5 mL). The filtrate was concentrated under vacuum to give 2-dimethylaminopyrimidine-5-carbaldehyde (427 mg, 97.7% yield) as a yellow solid. The product was analyzed by LC-MS (ES+) and showed a molecular ion peak [MH]+ of 152.2. HPLC analysis showed a retention time (Rt) of 4.14 min and a purity of 97.9%.

References

[1] Patent: US2015/258101, 2015, A1

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