4-Pyrimidinamine, 2-methoxy- (9CI) Chemical Properties

Melting point:

174 °C

Boiling point:

294.4±32.0 °C(Predicted)

Density 

1.224

storage temp. 

2-8°C(protect from light)

solubility 

DMSO: 60 mg/mL (479.50 mM)

pka

4.97±0.10(Predicted)

form 

solid

color 

White to off white

InChI

InChI=1S/C5H7N3O/c1-9-5-7-3-2-4(6)8-5/h2-3H,1H3,(H2,6,7,8)

InChIKey

DHYLZDVDOQLEAQ-UHFFFAOYSA-N

SMILES

C1(OC)=NC=CC(N)=N1

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36-36/37/38-20/21/22

Safety Statements 

26-36/37/39

WGK Germany 

3

HS Code 

29335990

4-Pyrimidinamine, 2-methoxy- (9CI) Usage And Synthesis

Uses

2-O-Methylcytosine, an O-alkylated analogue a DNA adduct, is the damaged nucleobase[1].

Definition

ChEBI: Pyrimidine substituted with a methoxy group at position C-2 and an amine group at C-4.

Synthesis

The general procedure for the synthesis of 4-amino-2-methoxypyrimidine from 2-chloro-4-aminopyrimidine is as follows: Pre-step A: Synthesis of 2-methoxy-4-pyrimidinamine 2-Chloro-4-pyrimidinamine (150 mg, 1.158 mmol) and sodium methanol (188 mg, 3.47 mmol) were dissolved in methanol (2.9 mL) and the mixture was heated to 100°C in a Biotage microwave reactor for 40 min. Upon completion of the reaction, the crude product was purified by reversed-phase high performance liquid chromatography (RP-HPLC) to afford 2-methoxy-4-pyrimidinamine (73 mg, 0.583 mmol, 50% yield). Mass spectrum (electrospray positive ion mode) m/z 126.0 ([M+H]+).

References

[1] Aliakbar Tehrani Z, et al. Comparison of gas phase intrinsic properties of cytosine and thymine nucleobases with their O-alkyl adducts: different hydrogen bonding preferences for thymine versus O-alkyl thymine. J Mol Model. 2013;19(8):2993‐3005. DOI:10.1007/s00894-013-1813-0

4-Pyrimidinamine, 2-methoxy- (9CI)(3289-47-2)Related Product Information

• 4-Amino-2-methoxy-phenol
• 2,4,6-Triaminopyrimidine
• 3'-Amino-4'-methoxyacetanilide
• p-Anisidine-3-sulfonic acid
• 2-Methoxyquinoline
• 3-CYANO-2-METHOXYPYRIDINE
• 2-Methoxybenzyl alcohol
• 2-NITRO-PYRIDIN-4-YLAMINE
• 4-AMINO-2,6-DICHLOROPHENOL HYDROCHLORIDE
• 4-AMINO-2,6-DIFLUOROPHENOL
• 2,6-DICHLORO-3-NITRO-4-AMINOPYRIDINE
• N2-ethylpyridine-2,4-diamine
• 4-Amino-2-(methylthio)pyrimidine-5-carbaldehyde
• 4-AMINO-2,6-DIBROMOPHENOL TIN(II)CHLORIDE HYDROCHLORIDE
• ethyl 4-amino-2-methylpyrimidine-5-carboxylate
• Pyrimidine