5437-49-0

Basic information

• Product Name: N~6~,N~6~-dimethyl-5H-purine-2,6-diamine
• CAS NO: 5437-49-0
• Molecular Formula: C₇H₁₀N₆
• Molecular Weight: 178.1945
• Mol File: 5437-49-0.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 306.8°C at 760 mmHg
• Flash Point: 139.3°C
• Density: 1.57g/cm³
• Vapor Pressure: 0.000756mmHg at 25°C
• Refractive Index: 1.781
• CAS DataBase Reference: N~6~,N~6~-dimethyl-5H-purine-2,6-diamine(CAS DataBase Reference)
• NIST Chemistry Reference: N~6~,N~6~-dimethyl-5H-purine-2,6-diamine(5437-49-0)
• EPA Substance Registry System: N~6~,N~6~-dimethyl-5H-purine-2,6-diamine(5437-49-0)

Safety Data

• Hazardous Substances Data: 5437-49-0(Hazardous Substances Data)

Upstream product

• 1198-47-6 6-Methylthioguanine 
• 124-40-3 dimethyl amine 
• 10310-21-1 2-Amino-6-chloropurin 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 402575-69-3 (S)-1-(2-Amino-6-dimethylamino-purin-9-yl)-3-trityloxy-propan-2-ol 

Relevant articles and documents

General method for nucleophilic aromatic substitution of aryl fluorides and chlorides with dimethylamine using hydroxide-assisted decomposition of N,N-dimethylforamide

A practical and convenient procedure for the nucleophilic aromatic substitution of aryl fluorides and chlorides with dimethylamine was developed using a hydroxide-assisted thermal decomposition of N,N-dimethylforamide. These conditions are tolerant of nitro, nitrile, aldehyde, ketone, and amide groups but will undergo acyl substitution to form amides for methyl esters and acyl chlorides. Isolated yields of the products range from 44% to 98%, with the majority being greater than 70% for 17 examples.

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.

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.