938-55-6

Basic information

• Product Name: 6-Dimethylaminopurine
• Synonyms: TIMTEC-BB SBB008765;N,N-DIMETHYL-N-(4-PYRIDINYL)AMINE;N,N'-DIMETHYL-4-PYRIDINAMINE;N6,N6-DIMETHYLADENINE;N4,N4-DIMETHYLPYRIDIN-4-AMINE;N-(4-PYRIDYL)DIMETHYLAMINE;DIMETHYLAMINO PYRIDINE;DIMETHYLAMINOPYRIDINE, 4-
• CAS NO: 938-55-6
• Molecular Formula: C₇H₉N₅
• Molecular Weight: 163.18
• EINECS: 214-353-5
• Product Categories: Nitrogen cyclic compounds;Purine;Nucleotides and Nucleosides;Bases & Related Reagents;Nucleotides
• Mol File: 938-55-6.mol

Chemical Properties

• Melting Point: 259-262 °C(lit.)
• Boiling Point: 162 °C (50 mmHg)
• Flash Point: 110 °C
• Appearance: off-white to yellow/prilled
• Density: 1.1407 (rough estimate)
• Vapor Pressure: 0.0154mmHg at 25°C
• Refractive Index: 1.6380 (estimate)
• Storage Temp.: −20°C
• Solubility: methanol: 0.1 g/mL, clear
• PKA: 9.38±0.20(Predicted)
• BRN: 7634
• CAS DataBase Reference: 6-Dimethylaminopurine(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Dimethylaminopurine(938-55-6)
• EPA Substance Registry System: 6-Dimethylaminopurine(938-55-6)

Safety Data

• Hazard Codes: T+
• Statements: 25-27-36/37/38
• Safety Statements: 26-28-36/37/39-45-24/25-22
• RIDADR: UN 2811 6.1/PG 1
• WGK Germany: 3
• RTECS: US9230000
• F: 10-23
• Hazardous Substances Data: 938-55-6(Hazardous Substances Data)

Usage

Uses

Used in Reproductive Biology:
6-Dimethylaminopurine is used as a regulator of oocyte maturation for artificially lengthening the pre-maturation period of oocyte growth. This is achieved by inhibiting germinal vesicle breakdown in both mouse and human oocytes, allowing for better control and understanding of the oocyte development process.
Used in Assisted Reproductive Technologies:
In the context of assisted reproductive technologies, 6-Dimethylaminopurine serves as a valuable tool for enhancing oocyte quality and maturation. By controlling the timing of germinal vesicle breakdown and meiotic maturation, it can potentially improve the success rates of in vitro fertilization and other related procedures.
Used in Research and Development:
6-Dimethylaminopurine is also utilized in research settings to study the mechanisms of oocyte maturation and the factors that influence it. This knowledge can contribute to the development of new strategies and techniques for improving fertility treatments and understanding reproductive biology.

Preparation

6-Dimethylaminopurine synthesis: 2-Methylmercapto-4-amino-6-dimethylaminopyrimidine (VI) was smoothly nitrosated in 10% acetic acid to the 5-nitrosopyrimidine (V) in 95% yield. Reduction of V with sodium hydrosulfite to the triamine (IV), followed by formylation gave the 5-formamidopyrimidine (VII) in 76% over-all yield for the two steps. Reductive formylation of V directly to VI1 with zinc and formic acid, although more rapid, was less efficient (50% yield). Ring closure of VII to 2-methyhercapto-6-dimethylaminopurine (X) was best done on a small scale by short fusion at 250°(99% yield), although boiling quinoline, formamide, or dilute alcoholic sodium hydroxide could also be employed. The latter reagent was most efficient on a large scale. Desulfurization of X with Raney nickel (7) in 1 N sodium hydroxide at 100° afforded the final product, 6-dimethylaminopurine (XII) in 43% yield.This compound was identical in all respects with the C7H9N5 moiety from puromycin (2).

Biochem/physiol Actions

6-(Dimethylamino)purine (6-DMAP) is a protein kinase and cyclin-dependent kinase inhibitor. It acts as a secondary metabolite and mediates RNA modification. 6-DMAP is a potent cytokinetic inhibitor and is used in parthenogenesis and meiosis studies. It is also used to promote pronuclei formation in mammalian oocytes. 6-DMAP is a dual fluorescence molecule according to femtosecond fluorescence up-conversion spectroscopy studies.

Purification Methods

It is purified by recrystallisation from H2O, EtOH (0.32g in 10mL) or CHCl3. [Albert & Brown J Chem Soc 2060 1954, UV: Mason J Chem Soc 2071 1954.] The monohydrochloride crystallises from EtOH/Et2O, m 2 5 3o(dec) [Elion et al. J Am Chem Soc 74 411 1952], the dihydrochloride has m 225o(dec) and the picrate has m 245o (235-236.5o) [Fryth et al. J Am Chem Soc 80 2736 1958]. [Beilstein 26 III/IV 3566.]

InChI:InChI=1/C7H9N5/c1-12(2)7-5-6(9-3-8-5)10-4-11-7/h3-5H,1-2H3

Upstream product

• 506-59-2 N,N-dimethylammonium chloride 
• 87-42-3 6-chloro-7H-purine 
• 68-94-0 Allopurinol 
• 81693-59-6 5-amino-4-(cyanoformimidoyl)-1H-imidazole 
• 124-40-3 dimethyl amine 
• 1188-33-6 N,N-dimethylformamide diethyl diacetal 
• 68-12-2 N,N-dimethyl-formamide 
• 87-42-3 6-chloropurine 
• 68-94-0 hypoxanthine 
• 81332-52-7 6-dimethylamino-9-(1-ethoxyethyl)purine 
• 35665-58-8 N⁶,N⁶-dimethyl-2'-deoxyadenosine 
• 99768-59-9 N-(4-amino-6-dimethylamino-2-methylsulfanyl-pyrimidin-5-yl)-formamide 
• 98335-73-0 N⁴,N⁴-dimethyl-2-methylsulfanyl-5-nitroso-pyrimidine-4,6-diyldiamine 
• 154-20-1 N⁴,N⁴-dimethyl-2-methylsulfanyl-pyrimidine-4,5,6-triyltriamine 

Downstream Products

• 86626-09-7 9-(2-benzoyloxypropyl-3-hydroxy)-6-dimethylaminopurine 
• 86626-11-1 9-(3-azido-2-benzoyloxypropyl)-6-dimethylaminopurine 
• 86626-08-6 9-(2-benzoyloxypropyl-3-benzyloxy)-6-dimethylaminopurine 
• 86626-13-3 9-(3-amino-2-hydroxypropyl)-6-dimethylaminopurine dihydrochloride 
• 86626-10-0 9-(2-benzoyloxypropyl-3-p-toluenesulfonyloxy)-6-dimethylaminopurine 
• 2620-62-4 N,N-dimethyladenosine 
• 124-40-3 dimethyl amine 
• 68-94-0 hypoxanthine 
• 132872-99-2 {(CO)Rh(μ-Dmad)(PPh3)}2*DMSO 
• 203569-36-2 ReCl₃(C₅H₃N₅(CH₃)2)2(P(C₆H₅)3) 
• 147361-89-5 Rh₂(HC(NC₆H₄CH₃)2)2(O₂CCF₃)2(C₅H₃N₄N(CH₃)2) 
• 147391-30-8 Rh₂(HC(NC₆H₄CH₃)2)2(O₂CCF₃)2(C₅H₃N₄N(CH₃)2)2 

Relevant articles and documents

Room-Temperature Amination of Chloroheteroarenes in Water by a Recyclable Copper(II)-Phosphaadamantanium Sulfonate System

Buchwald-Hartwig amination of chloroheteroarenes has been a challenging synthetic process, with very few protocols promoting this important transformation at ambient temperature. The current report discusses about an efficient copper-based catalytic system (Cu/PTABS) for the amination of chloroheteroarenes at ambient temperature in water as the sole reaction solvent, a combination that is first to be reported. A wide variety of chloroheteroarenes could be coupled efficiently with primary and secondary amines as well as selected amino acid esters under mild reaction conditions. Catalytic efficiency of the developed protocol also promotes late-stage functionalization of active pharmaceutical ingredients (APIs) such as antibiotics (floxacins) and anticancer drugs. The catalytic system also performs efficiently at a very low concentration of 0.0001 mol % (TON = 980,000) and can be recycled 12 times without any appreciable loss in activity. Theoretical calculations reveal that the π-acceptor ability of the ligand PTABS is the main reason for the appreciably high reactivity of the catalytic system. Preliminary characterization of the catalytic species in the reaction was carried out using UV-VIS and ESR spectroscopy, providing evidence for the Cu(II) oxidation state.

9-Sulfonyl-9(H)-Purine Derivatives Inhibit HCV Replication Via their Degradation Species

Cell-based screening of a privileged small molecule library led to the discovery of 9-sulfonyl-9(H)-purine as new scaffold for hepatitis C virus (HCV) inhibitors. Structure–activity relationship study with respect to the 2-, 6- and 9-positions in the purine core resulted in the identification of several active compounds with moderate potency against the HCV genotype 1b. Subsequent stability studies demonstrated that HCV inhibitors of this type were unstable in Dulbecco’s modified eagle medium (DMEM) and plasma, as well as glutathione-containing water, and their instability was closely related to their HCV inhibitory activity. A preliminary study of the mechanism of action showed that the sulfonamide bond at the 9-position of purine would be the primary degradation site and the resulting sulfonylation degradation species would mediate the anti-HCV activity of 9-sulfonyl-9(H)-purines. Results of this study demonstrated that 9-sulfonyl-9(H)-purine is an unstable scaffold for HCV inhibitors and further detailed analysis of the degradation species is needed to determine the main active components and direct target for this type of molecules.

The optimized microwave-assisted decomposition of formamides and its synthetic utility in the amination reactions of purines

The microwave-assisted decomposition of DMF was thoroughly studied and the reaction conditions (temperature, solvent effect, and effect of additives, such as acids, bases, and salts) were optimized for its use in amination reactions. The applicability of this expedient methodology in purine chemistry and with various formamides is demonstrated.

A new approach to the synthesis of N,N-dialkyladenine derivatives

N,N-Dialkyladenine derivatives were prepared by two different reaction sequences starting from 5-amino-4-cyanoformimidoylimidazoles. When these imidazoles were treated with dimethylformamide diethyl acetal, a 5-aminomethyleneamino-4-cyanoformimidoylimidazole was isolated and evolved to the N,N-dialkyladenine in the presence of a secondary alkylamine. The same purine structure was isolated when the 5-amino-4-cyanoformimidoylimidazole was first treated with a secondary amine to give a stable 4-amidino-5- aminoimidazole. The desired product was generated when the 4-amidino-5- aminoimidazole was combined with dimethylformamide diethyl acetal, at room temperature. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Convenient dimethylamino amination in heterocycles and aromatics with dimethylformamide

A convenient dimethylamino amination of various heterocyclic and aromatic compounds having activated chloro group has been carried out in good yields using dimethyl formamide (DMF).

Synthesis and cytostatic activity of N-[2-(phosphonomethoxy)alkyl] derivatives of N6-substituted adenines, 2,6-diaminopurines and related compounds

N6-Substituted adenine and 2,6-diaminopurine derivatives of 9-[2-(phosphonomethoxy)ethyl] (PME), 9-[(R)-2-(phosphonomethoxy)propyl] [(R)-PMP] and enantiomeric (S)-PMP series were synthesized by reactions of primary or secondary amines with 6-chloro-9-{[2-(diisopropoxyphosphoryl)methoxy]alkyl}purines (26-28) or 2-amino-6-chloro-9-{[2-(diisopropoxyphosphoryl)methoxy]alkyl}purines (29-31) followed by treatment of the diester intermediates 32 with bromo(trimethyl)silane and hydrolysis. Diesters 32 were also obtained by reaction of N6-substituted purines with synthons 23-25 bearing diisopropoxyphosphoryl group. Alkylation of 2-amino-6-chloropurine (9) with diethyl [2-(2-chloroethoxy)ethyl]phosphonate (148) gave the diester 149 which was analogously converted to N6-substituted 2,6-diamino-9-[2-(2-phosphonoethoxy)ethyl]purines 151-153. Alkylation of N6-substituted 2,6-diaminopurines with (R)-[(trityloxy)methyl]oxirane (155) followed by reaction of thus-obtained intermediates 156 with dimethylformamide dimethylacetal and condensation with diisopropyl [(tosyloxy)methyl]phosphonate (158) followed by deprotection of the intermediates 159 gave N6-substituted 2,6-diamino-9-[(S)-3-hydroxy-2-(phosphononiethoxy)propyl]purines 160-163. The highest cytostatic activity in vitro was exhibited by the following N6-derivatives of 2,6-diamino-9-[2-(phosphonomethoxy)ethyl]purine (PMEDAP): 2,2,2-trifluoroethyl (53), allyl (54), [(2-dimethylamino)ethyl] (68), cyclopropyl (75) and dimethyl (91). In CCRF-CEM cells, the cyclopropyl derivative 75 is deaminated to the guanine derivative PMEG (3) which is then converted to its diphosphate.

2'-Deoxypuromycin: Synthesis and antiviral evaluation

A new synthesis of 2'-deoxypuromycin (18) as well as its α-anomer 17 is described. Reaction of 1,5-di-O-acetyl-2,3-dideoxy-3-phthalimido-β-D-erythro-pentofuranose (3) with silylated 6-dimethylaminopurine using trimethylsilyl trifluoromethanesulfonate as catalyst afforded the α and β nucleosides 7 and 12 in 15 and 25% yield, respectively. After deblocking of both amino and hydroxy groups with methylamine in ethanol, the nucleosides were condensed with Fmoc-4-O-methyl-L-tyrosine and subsequently deprotected to give the target compounds 17 and 18. Compound 3 is converted into its glycosyl bromide 4 in quantitative yield on treatment with trimethylsilyl bromide, and reacted with the sodium salt of 6-dimethylaminopurine to give the corresponding protected N-7 and N-9 α glycosyl nucleosides 7 and 8 in 34 and 39% yield, respectively. The 2'-deoxypuromycin is inactive against HIV-1 in MT-4 cells.

ACIDIC HYDROLYSIS OF 6-SUBSTITUTED 9-(2-DEOXY-β-D-ERYTHRO-PENTOFURANOSYL)PURINES AND THEIR 9-(1-ALKOXYETHYL) COUNTERPARTS: KINETICS AND MECHANISM.

The rate constants for the hydrolysis of several 6-substituted 9-(2-deoxy-β-D-erythro-pentofuranosyl)purines and 9-(1-alkoxyethyl)purines have been measured at different concentrations of oxonium ion.The effects that varying the polar nature of the alkoxy group exerts on the hydrolysis of unsubstituted 9-(1-alkoxyethyl)purines are interpreted to indicate that the reaction proceeds by a rate-limiting departure of the protonated base moiety with a concomitant formation of an alkoxyethyl oxocarbenium ion.The same mechanism is applied to the hydrolysis of 9-(2-deoxy-β-D-erythro-pentofuranosyl)purines by comparing the influences that 6-substituents have on the reactivity of these compounds and their 9-(1-alkoxyethyl) counterparts.No sign of anomerisation was detected, when the hydrolysis of 2'-deoxyadenosine was followed by 1H NMR spectroscopy.

Preparation of 7-Substituted Pyrrolopyrimidines and 9-Substituted Purines as Potential Antiparasitic Agents

A series of six 7-substituted pyrrolopyrimidines and two 9-substituted purines were prepared and evaluated for potential antiparasitic activity.All were inactive against P. berghei in mice.Six of the target compounds were also evaluated for antitrypanosomal activity against T. rhodensiense in mice.All six compounds were also inactive in this screen.