132160-44-2

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 4397-53-9 p-benzyloxybenzaldehyde 
• 4195-25-9 2-amino-1-(4-benzyloxyphenyl)ethanone hydrochloride 
• 1266682-64-7 2-amino-5-benzoyl-4-[4-(methoxy)phenyl]-1H-pyrrole-3-carboxamide 
• 1266682-62-5 N-(2-(4-(benzyloxy)phenyl)-2-oxoethyl)methanesulfonamide 
• 1266682-68-1 6-[4-(benzyloxy)benzoyl]-5-[4-(benzyloxy)phenyl]-1H-pyrrolo[2,3-d]pyrimidine-2,4(3H,7H)-dione 
• 145745-01-3 6-(4-(Benzyloxy)benzoyl)-5-(4-(benzyloxy)phenyl)-1,3-bis((benzyloxy)methyl)-7-(2,4-dimethoxybenzyl)-2,4-dioxopyrrolo<2,3-d>pyrimidine 
• 145745-00-2 5-(4-(Benzyloxy)phenyl)-1,3-bis((benzyloxy)methyl)-7-(2,4-dimethoxybenzyl)-2,4-dioxopyrrolo<2,3-d>pyrimidine 
• 145745-02-4 6-(4-(Benzyloxy)benzoyl)-5-(4-(benzyloxy)phenyl)-1,3-bis((benzyloxy)methyl)-2,4-dioxopyrrolo<2,3-d>pyrimidine 
• 145744-99-6 1,3-Bis((benzyloxy)methyl)-7-(2,4-dimethoxybenzyl)-2,4-dioxo-5-((trifluoromethanesulfonyl)oxy)pyrrolo<2,3-d>pyrimidine 
• 145744-97-4 5-Acetoxy-1,3-bis((benzyloxy)methyl)-7-(2,4-dimethoxybenzyl)-2,4-dioxopyrrolo<2,3-d>pyrimidine 
• 145744-98-5 1,3-Bis((benzyloxy)methyl)-7-(2,4-dimethoxybenzyl)-2,4-dioxo-5-hydroxypyrrolo<2,3-d>pyrimidine 
• 145744-96-3 1,3-Bis((benzyloxy)methyl)-6-uracil 
• 175791-63-6 6--2,4-dimethoxy-7-phenylsulfonylpyrrolo<2,3-d>pyrimidine 

Downstream Products

• 132160-41-9 6-(4-Methoxy-benzoyl)-5-(4-methoxy-phenyl)-1,3,7-trimethyl-1,7-dihydro-pyrrolo[2,3-d]pyrimidine-2,4-dione 

Relevant academic research and scientific papers

Synthesis of Pyrrolo[2,3-d]pyrimidines by Copper-Mediated Carbomagnesiations of N-Sulfonyl Ynamides and Application to the Preparation of Rigidin A and a 7-Azaserotonin Derivative

The treatment of readily available N-alkynyl-5-iodo-6-sulfamido-pyrimidines with iPrMgCl?LiCl followed by a transmetalation with CuCN?2 LiCl produces, after intramolecular carbocupration, metalated pyrrolo[2,3-d]pyrimidines. Quenching of these pyrimidines with allylic halides or acid chlorides results in polyfunctional pyrrolo[2,3-d]pyrimidines. Further reaction with ICl and a Negishi cross-coupling, using PEPPSI-iPr as the catalyst, furnishes fully substituted N-heterocycles. A formal synthesis of the marine alkaloid rigidin A has been achieved as well as the preparation of a derivative of 7-azaserotonine, related to the natural hormone serotonin.

Exploring natural product chemistry and biology with multicomponent reactions. 5. Discovery of a novel tubulin-targeting scaffold derived from the rigidin family of marine alkaloids

We developed synthetic chemistry to access the marine alkaloid rigidins and over 40 synthetic analogues based on the 7-deazaxanthine, 7-deazaadenine, 7-deazapurine, and 7-deazahypoxanthine skeletons. Analogues based on the 7-deazahypoxanthine skeleton exh

One-pot multicomponent synthesis of diversely substituted 2-aminopyrroles. A short general synthesis of rigidins A, B, C, and D

Privileged medicinal scaffolds based on the structures of tetra-and pentasubstituted 2-aminopyrroles were prepared via one-pot multicomponent reactions of structurally diverse aldehydes and N-(aryl-, hetaryl-, alkylsulfonamido)acetophenones with activated methylene compounds. This methodology was used in a four-step synthesis of alkaloids rigidins A, B, C, and D in overall yields of 61%, 58%, 60%, and 53%, respectively. Of these, rigidins B, C, and D were synthesized for the first time.(Figure Presented)

The application of vinylogous iminium salt derivatives to an efficient synthesis of the pyrrole containing alkaloids Rigidin and Rigidin E

Studies directed on the synthesis of the pyrrole containing marine natural products Rigidin and Rigidin E via vinylogous iminium salts are described. The successful strategy relies on the formation of a 2,4-disubstituted pyrrole from a vinamidinium salt f

Condensed heteroaromatic ring systems. Part 24. Synthesis of rigidin, a pyrrolo[2,3-d]pynmidine marine alkaloid

The marine alkaloid rigidin has been synthesized from 2,4-dimethoxy-7-phenylsulfonylpyrrolo[2,3-d]-pyrimidine. Lithiation of the pyrrolo[2,3-d]pyrimidine followed by electrophilic substitution with N,4-dimethoxy-N-methylbenzainide afforded a 6-(4-methoxy)

TOTAL SYNTHESIS OF A MARINE ALKALOID, RIGIDIN

Rigidin, a marine alkaloid, was synthesized by the combination of acylation via lithiation and arylation by palladium-catalyzed reaction starting from 2,4-dimethoxypyrrolopyrimidine.

Synthesis of a Novel Pyrrolopyrimidine Alkaloid, Rigidin

An efficient nine-step synthesis of the brain phosphodiesterase inhibitor, rigidin, has been accomplished in 26percent overall yield starting from 6-chlorouracil and ethyl (2,4-dimethoxybenzyl)glycinate.A key feature of the synthetic route reveals a new m