175791-66-9

Upstream product

• 5720-07-0 4-methoxyphenylboronic acid 
• 175791-65-8 5-Iodo-2,4-dimethoxypyrrolo<2,3-d>pyrimidin-6-yl 4-methoxyphenyl ketone 
• 123-11-5 4-methoxy-benzaldehyde 
• 1009811-97-5 4,5-diiodo-2,6-dimethoxypyrimidine 
• 3551-55-1 2,4-dimethoxypyrimidine 
• 155826-85-0 4-methoxylphenylboronic acid 1,3-propanediol ester 
• 175791-63-6 6--2,4-dimethoxy-7-phenylsulfonylpyrrolo<2,3-d>pyrimidine 
• 155826-83-8 2,4-Dimethoxy-7-phenylsulfonylpyrrolo<2,3-d>pyrimidin-6-yl 4-methoxyphenyl ketone 
• 175791-64-7 2,4-Dimethoxypyrrolo<2,3-d>pyrimidin-6-yl 4-methoxyphenyl ketone 
• 155826-81-6 2,4-Dimethoxy-7-phenylsulfonylpyrrolo<2,3-d>pyrimidine 
• 52898-49-4 4,N-dimethoxy-N-methylbenzamide 
• 90057-09-3 2,4-dimethoxy-7H-pyrrolo<2,3-d>pyrimidine 

Downstream Products

• 132160-44-2 6-(4-hydroxybenzoyl)-5-(4-hydroxyphenyl)-1H-pyrrolo[2,3-d]pyrimidine-2,4(3H,7H)-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.

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.