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ChemicalBook--->CAS DataBase List--->3167-50-8

3167-50-8

3167-50-8 Structure

3167-50-8 Structure
IdentificationMore
[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 PropertiesBack 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)
Safety DataBack Directory
[Symbol(GHS) ]


GHS07
[Signal word ]

Warning
[Hazard statements ]

H315-H319-H335
[Precautionary statements ]

P261-P305+P351+P338
[Hazard Codes ]

Xi
[Risk Statements ]

20/21/22-36/37/38
[Safety Statements ]

36/37-24/25-22
[HS Code ]

29335990
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Ethyl acetate-->Sodium-->Potassium hydroxide-->Sodium hydride-->Guanidine hydrochloride-->Ethyl 3,3-Diethoxypropionate-->Propanoicacid,2-formyl-3-oxo-,ethylester-->METHYL 3,3-DIMETHOXYPROPIONATE-->Ethyl 2-aminopyrimidine-5-carboxylate-->Methyl formate
Spectrum DetailBack Directory
[Spectrum Detail]

2-Aminopyrimidine-5-carboxylic acid(3167-50-8)1HNMR
Hazard InformationBack 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]

Ethyl 2-aminopyrimidine-5-carboxylate

308348-93-8

2-Aminopyrimidine-5-carboxylic acid

3167-50-8

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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