708-74-7

Usage

Uses

Used in Pharmaceutical Synthesis:
2,4-Pteridinediamine,6-methylis used as a key intermediate in the synthesis of various pharmaceuticals due to its unique chemical structure and reactivity.
Used in Dye Production:
In the dye industry, 2,4-Pteridinediamine,6-methylis utilized as a precursor for the production of dyes, capitalizing on its chemical properties to create a range of colorants.
Used in Cancer Treatment Research:
2,4-Pteridinediamine,6-methylis studied for its potential role in cancer treatment, with ongoing research exploring its effects on tumor growth and progression.
Used in Diabetes Management Research:
2,4-Pteridinediamine,6-methylis also being investigated for its possible applications in diabetes management, with research focusing on its impact on blood sugar levels and related metabolic pathways.
Used in Antioxidant and Anti-Inflammatory Applications:
2,4-Pteridinediamine,6-methylis employed in the development of antioxidants and anti-inflammatory agents, leveraging its inherent properties to combat oxidative stress and inflammation in various medical conditions.

InChI:InChI=1/C7H8N6/c1-3-2-10-6-4(11-3)5(8)12-7(9)13-6/h2H,1H3,(H4,8,9,10,12,13)

Upstream product

• 1004-74-6 2,4,5,6-tetraaminopyrimidine 
• 73323-67-8 N-acetyl-α-aminopropionaldehyde 
• 79614-35-0 1-(benzenesulfonyl)-4-methylimidazolin-2-one 
• 83736-00-9 1-(4-Fluoro-benzenesulfonyl)-4-methyl-1,3-dihydro-imidazol-2-one 
• 79614-36-1 1-(4'-chlorobenzenesulfonyl)-4-methylimidazolin-2-one 
• 83736-03-2 1-(4-Bromo-benzenesulfonyl)-4-methyl-1,3-dihydro-imidazol-2-one 
• 83735-99-3 1-(4-Methoxy-benzenesulfonyl)-4-methyl-1,3-dihydro-imidazol-2-one 
• 83736-01-0 1-(2,5-Dichloro-benzenesulfonyl)-4-methyl-1,3-dihydro-imidazol-2-one 
• 83736-02-1 1-(2,5-Dibromo-benzenesulfonyl)-4-methyl-1,3-dihydro-imidazol-2-one 
• 54972-20-2 1-tosyl-4-methylimidazolin-2-one 
• 867-54-9 1,1-dibromopropan-2-one 
• 5392-28-9 2,4,5,6-tetraaminopyrimidine sulfate 
• 152941-77-0 4-amino-6-methyl-2-pivaloylaminopteridine 
• 39944-62-2 2,4,5,6-tetraamino-pyrimidine dihydrochloride 

Downstream Products

• 708-75-8 2-amino-6-methylpteridin-4(1H)-one 
• 86669-33-2 methotrexate di-t-butyl ester 
• 113311-25-4 2,4-diamino-6-dibromomethylpteridine 
• 59368-16-0 6-bromomethyl-pteridine-2,4-diamine 
• 59-05-2 N-[4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-L-glutamic acid 

Relevant academic research and scientific papers

One-step synthesis of lumazine and xanthine: First co-crystal of lumazine and perchloric acid with a unique monohydrated hydronium ion (H 5O2+) mediated supramolecular assembly of the lumazine dimer

A perchloric acid mediated one-step synthesis of lumazine derivatives from pterins and xanthine from guanine is reported. However, 2-pivaloylamino derivatives of pterins underwent simple hydrolysis of the pivaloylamino group generating free pterin compounds, but the 2-oxo derivatives, that is, the lumazine compounds, were not obtained. A novel supramolecular assembly is constructed by the unique hydrogen bonding of H5O2 + bridging two hydrogen-bonded dimers of lumazine to form the co-crystal 21 with aqueous perchloric acid. In contrast, N2-pivaloyl- 6-bromo-5-deazapterin was simply hydrolysed to form the protonated deazapterin 22, which forms a unique six-membered cyclic hydrogen-bonded structure leading to the generation of a polymeric supramolecular assembly. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

A new, general and regioselective method for the synthesis of 2,6-disubstituted 4-aminopteridines

A new synthetic method for the preparation of 2,6-disubstituted 4-aminopteridines is described. Treatment of a-substituted 4,5,6-triaminopyrimidines with α-ketoaldoximes in MeOH affords in a regioselective one-step reaction 2,6-disubstituted 4-aminopteridines in high yield.

PROTECTION AND DEPROTECTION OF FUSED 2-AMINO-4(3H)PYRIMIDONES: CONVERSION OF PTERINS AND 5-DEAZAPTERINS TO 2,4-DIAMINO DERIVATIVES

5-Deazapterins and pterins are readily converted to their 4-deoxy-4-amino derivatives (a lactam-to-amidine conversion) by reaction with 4-chlorophenyl phosphorodichloridate and 1,2,4-triazole to give intermediate 4- derivatives, followed by reaction with aqueous ammonia.Some anomalous results obtained by application of the Mitsunobu reaction (normally a lactam-to-lactim ether conversion) to 5-deazapterins are detailed.

Process for the production of methotrexate

Process for the production of methotrexate, which is N[p-([(2,4-diamino-6-pteridyl)-methyl]-N10 -methylamino)-benzoyl]-L-glutamic acid. The process includes converting 1,1-dichloroacetone with 2,4,5,6-tetraaminopyrimidine in the presence of sodium bisulfite at a constant pH between 3.5 and 5 and at a temperature between 10° and 100° C. The resultant 2,4-diamino-6-methylpteridine is converted in a reaction medium with bromide. 0.3 to 1.0 ml of bromine is used per 1.0 g of the 2,4-diamino-6-methylpteridine. The 2,4-diamino-6-bromo methyl pteridine is converted with p-(N-methyl)-aminobenzoyl-L-glutamic acid or a salt thereof in a polar reaction medium into methoxtrexate.