2-Aminopyrimidine-5-carboxylic acid Chemical Properties

Melting point:

>300 °C

Boiling point:

474.6±37.0 °C(Predicted)

Density 

1.533±0.06 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

pka

4.19±0.10(Predicted)

Appearance

White to yellow Solid

InChI

InChI=1S/C5H5N3O2/c6-5-7-1-3(2-8-5)4(9)10/h1-2H,(H,9,10)(H2,6,7,8)

InChIKey

CBRLWSXYXSFYSP-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

3167-50-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

20/21/22-36/37/38

Safety Statements 

36/37-24/25-22

HS Code 

29335990

2-Aminopyrimidine-5-carboxylic acid Usage And Synthesis

Reactivity Profile

Decarboxylative Csingle bondC cross-couplings of 2-aminopyrimidine-5-carboxylic acids under a Pd/Ag-based catalytic system opens a new platform for introducing diverse C5 substituents. The reaction methods proceeded efficiently with various acids and the coupling partners of aryl iodides, alkenes, bromoalkynes, and azoles.

Synthesis

General procedure for the synthesis of 2-aminopyrimidine-5-carboxylic acid from methyl 2-aminopyrimidine-5-carboxylate: methyl 2-aminopyrimidine-5-carboxylate (300 mg, 2.0 mmol) was dissolved in methanol (5 mL) containing a small amount of water. Lithium hydroxide (122 mg, 5.1 mmol) was added to the solution and the reaction mixture was subsequently stirred at 60 °C overnight. Upon completion of the reaction, the mixture was concentrated under reduced pressure, and the residue was diluted with water and the pH was adjusted to 4 with 1 M HCl solution.At this point, 2-aminopyrimidine-5-carboxylic acid precipitated as a white solid, and the product was collected by filtration under vacuum to give 244 mg in 90% yield. The product was characterized by 1H NMR (DMSO-d6): δ 12.73 (1H, broad peak), 8.63 (2H, single peak), 7.44 (2H, broad peak).

References

[1] Ngoc Son Le Pham . “Decarboxylative cross-couplings of 2-aminopyrimidine-5-carboxylic acids.” Tetrahedron 74 28 (2018): Pages 3843-3851.

2-Aminopyrimidine-5-carboxylic acid(3167-50-8)Related Product Information

• 2-AMINO-PYRIMIDINE-5-CARBOXYLIC ACID ETHYL ESTER
• 2-Aminotoluene-5-sulfonic acid
• 6-Aminopyridine-2-carboxylic acid
• 4-AMINO-2-(TRIFLUOROMETHYL)PYRIMIDINE-5-CARBOXYLIC ACID
• 6-AMINO-5-NITROPYRIMIDIN-4-OL
• ETHYL 2-AMINO-4-(TRIFLUOROMETHYL)PYRIMIDINE-5-CARBOXYLATE
• ETHYL 2-AMINO-4-PROPYLPYRIMIDINE-5-CARBOXYLATE
• 2-AMINO-5-CARBOETHOXY-4-HYDROXYPYRIMIDINE
• ETHYL 2-AMINO-4-METHYLPYRIMIDINE-5-CARBOXYLATE
• Methyl 2-aminopyridine-4-carboxylate
• 2,4-DIAMINOPYRIMIDINE-5-CARBOXYLIC ACID
• 6-AMINO-PYRIMIDINE-4-CARBOXYLIC ACID
• 5-AMINO-PYRIMIDINE-2-CARBOXYLIC ACID
• ETHYL 4-(4-FLUOROPHENYL)-6-ISOPROPYL-2-(N-METHYLMETHYLSULFONAMIDO)PYRIMIDINE-5-CARBOXYLATE-D6
• 5-Aminopyrimidine-4-carboxylic acid
• 4-AMINOPYRIMIDINE-5-CARBOXYLIC ACID
• 2-AMINO-PYRIMIDINE-4-CARBOXYLIC ACID
• 4-AMINO-2-METHYL-PYRIMIDINE-5-CARBOXYLIC ACID