204770-73-0

Basic information

• Product Name: (4S)-2-(2'',4''-dimethoxybenzyl)-4-methyl-2,3,4,6-tetrahydro-1H-pyrazino[2,1-b]quinazoline-3,6-dione
• CAS NO: 204770-73-0
• Molecular Weight: 379.415
• Mol File: 204770-73-0.mol

Chemical Properties

• CAS DataBase Reference: (4S)-2-(2'',4''-dimethoxybenzyl)-4-methyl-2,3,4,6-tetrahydro-1H-pyrazino[2,1-b]quinazoline-3,6-dione(CAS DataBase Reference)
• NIST Chemistry Reference: (4S)-2-(2'',4''-dimethoxybenzyl)-4-methyl-2,3,4,6-tetrahydro-1H-pyrazino[2,1-b]quinazoline-3,6-dione(204770-73-0)
• EPA Substance Registry System: (4S)-2-(2'',4''-dimethoxybenzyl)-4-methyl-2,3,4,6-tetrahydro-1H-pyrazino[2,1-b]quinazoline-3,6-dione(204770-73-0)

Safety Data

• Hazardous Substances Data: 204770-73-0(Hazardous Substances Data)

Upstream product

• 204770-72-9 (S)-1-(2,4-dimethoxybenzyl)-3-methylpiperazine-2,5-dione 
• 95218-34-1 ethyl 2-{[(2,4-dimethoxyphenyl)methyl]amino}acetate 
• 300766-79-4 (3S,6S)-1-(o-azidobenzoyl)-4-(2'',4''-dimethoxybenzyl)-3-(3'-indolylmethyl)-6-methyl-2,5-piperazinedione 
• 300766-84-1 methyl N-tert-butoxycarbonyl-N'-(2'',4''-dimethoxybenzyl)-(S)-alanyl-(S)-tryptophanate 
• 300766-86-3 (3S,6S)-6-(3'-indolylmethyl)-3-methyl-1-(2,4-dimethoxybenzyl)-2,5-piperazinedione 
• 168766-64-1 methyl (S)-N'-(2,4-dimethoxybenzyl)tryptophanate 
• 613-45-6 2,4-Dimethoxybenzaldehyde 
• 34897-85-3 o-azidobenzoyl chloride 
• 300766-81-8 (1S,4S)-2-(2'',4''-dimethoxybenzyl)-1-(3'-indolylmethyl)-4-methyl-2,3,4,6-tetrahydro-1H-pyrazino[2,1-b]quinazoline-3,6-dione 
• 118-92-3 anthranilic acid 

Downstream Products

• 204771-42-6 (1R,4S)-2-(2,4-Dimethoxy-benzyl)-4-methyl-1-(4-methyl-benzyl)-1,2-dihydro-2,4a,9-triaza-anthracene-3,10-dione 

Relevant articles and documents

Synthesis of a seco analogue of ardeemin

(1S,4S)-1-Indolylmethyl-4-methyl-2,4-dihydro-1H-pyrazino[2,1-b]-q uinazaline-3,6-dione, a seco analogue of ardeemin, was synthesized in six steps from L-tryptophan methyl ester via an N-protected 2,5-piperazinedione and using an aza-Wittig reaction for the preparation of the quinazoline system. The final acid-promoted deprotection required tuning of the reaction conditions in order to minimize a side reaction involving loss of the indolylmethyl side chain.

New findings in the alkylation and N-deprotection of (4S)-4-methyl-2- benzyl-2,4-dihydro-1H-pyrazino [2,1-b] quinazoline-3,6-diones

Alkyl halides behave differently to benzyl halides in C-1 alkylation of the title compounds. The syn and anti 1,4-disubstituted diastereomers thus obtained show different regioselectivity by further alkylation leading to the 1,4,4-and 1,1,4-trisubstituted compounds, respectively. Alkylation is always directed anti with respect to the bulkier substituent at C-l or C-4. Debenzylation attempts on 2-benzyl-derivatives lb by treatment with HCOOH and C/Pd or H2/C-Pd/MeOH/H+ led to C-1 oxidised or 7,8,9,10-tetrahydro- derivatives. Deprotection of 2-p-methoxybenzyland 2-(2,4-dimethoxybenzyl)- derivatives with CAN and with TFA/anisole, respectively, was successful, but in the latter case epimerization at C-1 occurred.