Identification | Back Directory | [Name]
1-METHYLCYTOSIN | [CAS]
1122-47-0 | [Synonyms]
NSC 47693 1-METHYLCYTOSIN 1-METHYLCYTOSINE N1-Methylcytosine RARECHEM AQ NN 0292 4-amino-1-methylpyrimidin-2-one 4-amino-1-methyl-pyrimidin-2-one 4-azanyl-1-methyl-pyrimidin-2-one 4-aMino-1-MethylpyriMidin-2(1H)-one 4-AMino-1-Methyl-1H-pyriMidin-2-one 4-Amino-1-methyl-2(1H)-pyrimidinone 2(1H)-Pyrimidinone,4-amino-1-methyl- 1-Methyl-4-aminopyrimidine-2(1H)-one 1-Methyl-4-amino-1,2-dihydropyrimidine-2-one 1-Methyl-4-imino-1,2,3,4-tetrahydropyrimidine-2-one 1-Methyl-1,2,3,4-tetrahydro-4-iminopyrimidine-2-one | [Molecular Formula]
C5H7N3O | [MDL Number]
MFCD00038058 | [MOL File]
1122-47-0.mol | [Molecular Weight]
125.13 |
Chemical Properties | Back Directory | [Melting point ]
300-303℃ | [Boiling point ]
242℃ | [density ]
1.34 | [Fp ]
100℃ | [storage temp. ]
Keep in dark place,Sealed in dry,2-8°C | [solubility ]
Methanol (Slightly), Water (Slightly) | [form ]
Solid | [pka]
4.53±0.10(Predicted) | [color ]
White to Off-White |
Hazard Information | Back Directory | [Uses]
1-Methylcytosine is a methylated form of the DNA base cytosine and used as a nucleobase of hachimoji DNA, in which it pairs with Isoguanine[1][2]. | [Definition]
ChEBI: A pyrimidone that is cytosine in which the hydrogen attached to the nitrogen at position 1 is substituted by a methyl group. | [Synthesis]
4-N-(N,N-dimethylaminomethylene)-1-methylcytosine (1.0 g, 5.5 mmol) was added to a 100 mL round bottom flask equipped with a magnetic stirrer along with an ethanol solution (50 mL) containing 30% methylamine. The reaction mixture was stirred at room temperature for 12 hours. Upon completion of the reaction, the precipitated white solid was collected by filtration and purified by recrystallization using ethanol-water solvent mixture. 4-Amino-1-methylpyrimidin-2(1H)-one was finally obtained as a white solid (0.61 g, 88% yield). The structure of the product was analyzed by 1H NMR (400 MHz, DMSO-d6): δ3.31 (s, 3H), 5.59 (d, 1H), 6.91 (br, 2H), 7.54 (d, 1H); 13C NMR (100 MHz, DMSO-d6): δ6.6, 92.9, 146.6, 156.3, 166.1; mass spectrometry (ES+) ) analysis: calculated value C5H7N3O+ (M+H+) 126.0662, measured value 126.0804 confirmed. | [References]
[1] Kistenmacher, T. J.; Rossi, M. (1977-12-15). "1-Methylcytosine: a refinement". Acta Crystallographica (1977) Section B. 33 (12): 3962–3965. [2] Hoshika S, et al. Hachimoji DNA and RNA: A genetic system with eight building blocks. Science. 2019 Feb 22;363(6429):884-887. DOI:10.1126/science.aat0971 |
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