6-(METHYLAMINO)PURINE

Product Name6-(METHYLAMINO)PURINE
CAS443-72-1
MFC6H7N5
MW149.15
EINECS207-137-7
MOL File443-72-1.mol

Chemical Properties

Melting point	≥300 °C
Boiling point	256.3±50.0 °C(Predicted)
Density	1.57±0.1 g/cm3(Predicted)
storage temp.	Keep in dark place,Sealed in dry,Room Temperature
solubility	DMSO (Slightly, Heated), Methanol (Slightly, Heated)
form	Solid
pka	9.61±0.20(Predicted)
color	White to Light Grey
Major Application	general analytical life science and biopharma metabolomics
InChI	InChI=1S/C6H7N5/c1-7-5-4-6(10-2-8-4)11-3-9-5/h2-3H,1H3,(H2,7,8,9,10,11)
InChIKey	CKOMXBHMKXXTNW-UHFFFAOYSA-N
SMILES	N1=CN=C(NC)C=2NC=NC12
CAS DataBase Reference	443-72-1

Safety Information

WGK Germany	3
F	10-23
HS Code	2933998090

MSDS

Provider	Language
SigmaAldrich	English

Usage And Synthesis

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.

Uses

6-(Methylamino)purine, 6-methylade is a reagent for substitution of adenine nucleotide analogs containing bicyclohexane ring system locked in northern conformation enhanced potency as py receptor antagonists. Adenine methylation as an epigenic mark has been observed in single-celled organisms and also rarely in mamalian cells.

Definition

ChEBI: A 6-alkylaminopurine that is 9H-purin-6-amine substituted by a methyl group at the amino nitrogen.

Synthesis

87-42-3

74-89-5

443-72-1

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

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

Preparation Products And Raw materials

6-(METHYLAMINO)PURINE Supplier

6-(METHYLAMINO)PURINE manufacturers

Related Product Information

Send Inquriy