| Identification | Back Directory | [Name]
4-Pyrimidinamine, 2-methoxy- (9CI) | [CAS]
3289-47-2 | [Synonyms]
2-Methoxycytosine
2-O-Methylcytosine
2-methoxypyrimidin-4-amine
2-Methoxy-4-PyriMidinaMine
4-AMINO-2-METHOXYPYRIMIDINE
4-Pyrimidinamine, 2-methoxy-
(2-methoxypyrimidin-4-yl)amine
2-methoxypyrimidin-4(3H)-imine
4-Pyrimidinamine, 2-methoxy- (9CI)
4-Pyrimidinamine, 2-methoxy- (9CI) ISO 9001：2015 REACH
2-Methoxypyrimidin-4-amine, 4-Amino-2-methoxy-1,3-diazine | [Molecular Formula]
C5H7N3O | [MDL Number]
MFCD00128201
| [MOL File]
3289-47-2.mol | [Molecular Weight]
125.129 |
| Chemical Properties | Back Directory | [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) | [form ]
solid | [pka]
4.97±0.10(Predicted) | [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 |
| Hazard Information | Back Directory | [Definition]
ChEBI: Pyrimidine substituted with a methoxy group at position C-2 and an amine group at C-4. | [Uses]
2-O-Methylcytosine, an O-alkylated analogue a DNA adduct, is the damaged nucleobase[1]. | [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 |
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