160516-13-2

Upstream product

• 1928-76-3 9-benzyl-6-chloro-9H-purine 
• 75-16-1 methylmagnesium bromide 
• 4949-44-4 ethyl propanoylacetate 
• 105-53-3 diethyl malonate 
• 123-54-6 acetylacetone 
• 141-97-9 ethyl acetoacetate 
• 83135-13-1 9-benzyl-6-iodo-9H-purine 
• 87-42-3 6-chloropurine 
• 100-44-7 benzyl chloride 
• 333780-81-7 9-benzyl-6-ethynyl-9H-purine 

Relevant academic research and scientific papers

Synthesis of purines bearing functionalized C-substituents by the conjugate addition of nucleophiles to 6-vinylpurines and 6-ethynylpurines

Purines bearing diverse β-substituted ethyl or vinyl groups in position 6 were prepared by the conjugate addition of N-, O- and S-nucleophiles to 6-vinylpurines or 6-ethynylpurines. The scope of this methodology was systematically studied. The addition of

Microwave promoted C6-alkylation of purines through SNAr-based reaction of 6-chloropurines with 3-alkyl-acetylacetone

C6-Alkylated purine analogues were obtained in good to excellent isolated yields by SNAr reaction of 6-chloropurine derivatives with 3-alkyl-acetylacetone. 3-Alkyl-acetylacetones were employed as alkylating agents and C6-alkylated purines were obtained highly selectively within short reaction time under microwave irradiation conditions. This work is complementary to the classical coupling reactions for the synthesis of C6-alkylated purine analogues.

Improved one-pot synthesis of 6-methylpurines under microwave irradiation

A facile and efficient method for direct synthesis of 6-methylpurines was developed through SNAr-based addition reactions between various 6-halopurine derivatives and ethyl acetoacetate with assistance of microwave irradiation, which underwent direct coupling reaction, in situ deacetylation and decarboxylation to yield 6-methylated purines in high to excellent yields within 10 min. ARKAT USA, Inc.

Cross-coupling reactions of halopurines with aryl- and alkyltrifluoroborates; the scope and limitations in the synthesis of modified purines

The scope and limitations of the use of the palladium-catalyzed cross-coupling reactions of diverse alkyl- and aryltrifluoroborates with halopurines have been studied. While aryl- and hetaryltrifluoroborates reacted readily with both 6-chloropurines and 8

Synthesis of (purin-6-yl)acetates and their transformations to 6-(2-hydroxyethyl)-and 6-(carbamoylmethyl)purines

A novel approach to the synthesis of (purin-6-yl)acetates was developed based on Pdcatalyzed cross-coupling reactions of 6-chloropurines with a Reformatsky reagent. Their reduction with NaBH4 and treatment with MnO2 gave 6-(2-hydroxyethyl)purines, while reactions with amines in presence of NaCN afforded 6-(carbamoylmethyl)purines. Mesylation of the 6-(2-hydroxyethyl)purines followed by nucleophilic substitutions gave rise to several 6-(2-substituted ethyl)purines. This methodology was successfully applied to the synthesis of substituted purine bases and nucleosides for cytostatic and antiviral activity screening. None of the compounds exerted significant activity.

Straightforward and highly efficient catalyst-free one-step synthesis of 2-(purin-6-yl)acetoacetic acid ethyl esters, (purin-6-yl)acetates, and 6-methylpurines through SNAr-based reactions of 6-halopurines with ethyl acetoacetate

A novel approach to the synthesis of purines bearing functlonallzed carbon substltuents or methyl In position 6 was developed. Under different reaction conditions, 6-halopurlne derivatives could react with ethyl acetoacetate efficiently to yield 2-(purln-

6-Halopurines in palladium-catalyzed coupling with organotin and organozinc reagents

N-9 and N-7 benzylated 6-halopurines readily participate in palladium catalyzed cross coupling reactions with organotin and organozinc derivatives. In most instances the 6-chloropurines can be used. Organostannanes are excellent reagents for the introduction of alkenyl and aryl substituents, but organozinc compounds are the reagents of choice for the introduction of alkyl groups.