| Identification | More | [Name]
2-Aminopyrimidine-5-carboxylic acid | [CAS]
3167-50-8 | [Synonyms]
2-AMINOPYRIMIDINE-5-CARBOXYLIC ACID
ASISCHEM C63548
2-Aminopyrimidine-5-carboxylicacid95%
5-Pyrimidinecarboxylic acid, 2-amino-(7CI,8CI,9CI) | [Molecular Formula]
C5H5N3O2 | [MDL Number]
MFCD05864791 | [Molecular Weight]
139.11 | [MOL File]
3167-50-8.mol |
| Chemical Properties | Back Directory | [Melting point ]
>300 °C | [Boiling point ]
474.6±37.0 °C(Predicted) | [density ]
1.533±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,2-8°C | [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) |
| Hazard Information | Back Directory | [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.
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