| Identification | Back Directory | [Name]
6-(METHYLAMINO)PURINE | [CAS]
443-72-1 | [Synonyms]
N-METHYLADENINE
6-Methyladenine
N6-METHYLADENINE
N6-Methylademine
Adenine, N-methyl-
N6-Monomethyladenine
6-(METHYLAMINO)PURINE
N(Sup6)-Methyladenine
6-Monomethylaminopurine
6-Methylamino-7H-purine
methyl(purin-6-yl)amine
N-Methyl-1H-purin-6-amine
N-methyl-7H-purin-6-amine
N(Sup6)-Monomethyladenine
N-Methyl-9H-purin-6-amine
6-(METHYLAMINO)PURINE 99+%
9H-Purin-6-aMine, N-Methyl-
1H-Purin-6-amine, N-methyl-
Methyl-(7H-purin-6-yl)-amine
1H-Purin-6-amine, N-methyl- (9CI)
6-(Methylamino)purine, N-Methyladenine | [EINECS(EC#)]
207-137-7 | [Molecular Formula]
C6H7N5 | [MDL Number]
MFCD00075820 | [MOL File]
443-72-1.mol | [Molecular Weight]
149.15 |
| Chemical Properties | Back Directory | [Melting point ]
≥300 °C
| [Boiling point ]
256.3±50.0 °C(Predicted) | [density ]
1.57±0.1 g/cm3(Predicted) | [storage temp. ]
2-8°C | [solubility ]
DMSO (Slightly, Heated), Methanol (Slightly, Heated) | [form ]
Solid | [pka]
9.61±0.20(Predicted) | [color ]
White to Light Grey | [CAS DataBase Reference]
443-72-1 |
| Hazard Information | Back Directory | [Uses]
N6-Methyladenine is a modified purine that is commonly found in genomes of prokaryotes, protists, and plants. It is less common in higher eukaryotes and extremely rare in mammals. Like methylation of other DNA residues, N6-methyladenine represents an epigenetic modification that can affect diverse DNA functions, including replication, repair, and expression. | [Definition]
ChEBI: A 6-alkylaminopurine that is 9H-purin-6-amine substituted by a methyl group at the amino nitrogen. | [Synthesis]
Example 147 Steps for the synthesis of 1-[4-(6-(methylamino)purin-9-yl)phenyl]-3-[3-(4-methylpiperazin-1-ylmethyl)-5-(trifluoromethyl)phenyl]urea (Table 2, compound 25):
Step A Preparation of 6-methylaminopurine
Dissolve 12.5 g (79 mmol) of 6-chloropurine in 20 mL of 40% methanol solution of methylamine and 20 mL of ethanol. The reaction solution was sealed in a reaction tube and stirred at 120 °C for 4 hours. After completion of the reaction, the reaction solution was concentrated, ground with water, filtered to collect the solid, washed with water and dried under vacuum to give 10.78 g (90% yield) of 6-methylaminopurine as a white solid.
1H-NMR (270 MHz, DMSO-d6) δ (ppm): 2.98 (3H, br.s), 7.58 (1H, br.s), 8.06 (1H, s), 8.19 (1H, br.s), 12.89 (1H, br.s).
ESI (LC-MS positive mode) m/z 150 (M + H). | [IC 50]
Human Endogenous Metabolite | [storage]
Store at -20°C | [Purification Methods]
The purine is best purified by recrystallising 2g from 50mL of H2O and 1.2g of charcoal. [UV: Albert & Brown J Chem Soc 2060 1954; UV: Mason J Chem Soc 2071 1954; see also Elion et al. J Am Chem Soc 74 411 1952.] The picrate has m 265o(257o) [Bredereck et al. Chem Ber 81 307 1948]. [Beilstein 26 III/IV 3565.] | [References]
[1] Patent: EP1724258, 2006, A1. Location in patent: Page/Page column 138 |
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WG reagent
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