methyl 2-benzyl-8-methoxy-1-oxo-1,2,3,4,4a,5-hexahydropyrimido[1,6-a]indole-7-carboxylate

Base Information

Chemical Name:methyl 2-benzyl-8-methoxy-1-oxo-1,2,3,4,4a,5-hexahydropyrimido[1,6-a]indole-7-carboxylate
CAS No.:1352448-82-8
Molecular Formula:C₂₁H₂₂N₂O₄
Molecular Weight:366.417
Hs Code.:

Synonyms:methyl 2-benzyl-8-methoxy-1-oxo-1,2,3,4,4a,5-hexahydropyrimido[1,6-a]indole-7-carboxylate

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Chemical Property of methyl 2-benzyl-8-methoxy-1-oxo-1,2,3,4,4a,5-hexahydropyrimido[1,6-a]indole-7-carboxylate

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Technology Process of methyl 2-benzyl-8-methoxy-1-oxo-1,2,3,4,4a,5-hexahydropyrimido[1,6-a]indole-7-carboxylate

There total 3 articles about methyl 2-benzyl-8-methoxy-1-oxo-1,2,3,4,4a,5-hexahydropyrimido[1,6-a]indole-7-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 61.0%

: 1352448-44-2
methyl 4-(3-benzyl-6-methyl-2-oxotetrahydropyrimidin-1(2H)-yl)-5-bromo-2-methoxybenzoate

: 1352448-82-8
methyl 2-benzyl-8-methoxy-1-oxo-1,2,3,4,4a,5-hexahydropyrimido[1,6-a]indole-7-carboxylate

Guidance literature:: With palladium⁽⁰⁾bis(tricyclohexylphosphine); sodium carbonate; potassium carbonate; Trimethylacetic acid; In toluene; at 140 ℃; for 48h;
DOI:10.1021/ol2031763

Reference yield:

: 1352448-60-2
methyl 4-(3-benzyl-6-methyl-2-oxotetrahydropyrimidin-1(2H)-yl)-2-methoxybenzoate

: 1352448-82-8
methyl 2-benzyl-8-methoxy-1-oxo-1,2,3,4,4a,5-hexahydropyrimido[1,6-a]indole-7-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: N-Bromosuccinimide / N,N-dimethyl-formamide / 20 - 60 °C

2: palladium⁽⁰⁾bis(tricyclohexylphosphine); sodium carbonate; potassium carbonate; Trimethylacetic acid / toluene / 48 h / 140 °C

With N-Bromosuccinimide; palladium⁽⁰⁾bis(tricyclohexylphosphine); sodium carbonate; potassium carbonate; Trimethylacetic acid; In N,N-dimethyl-formamide; toluene;
DOI:10.1021/ol2031763

Reference yield:

: 1352448-28-2
1-benzyl-4-methyltetrahydropyrimidin-2(1H)-one

: 1352448-82-8
methyl 2-benzyl-8-methoxy-1-oxo-1,2,3,4,4a,5-hexahydropyrimido[1,6-a]indole-7-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene / 1,4-dioxane / 100 °C / Inert atmosphere

2: N-Bromosuccinimide / N,N-dimethyl-formamide / 20 - 60 °C

3: palladium⁽⁰⁾bis(tricyclohexylphosphine); sodium carbonate; potassium carbonate; Trimethylacetic acid / toluene / 48 h / 140 °C

With N-Bromosuccinimide; palladium⁽⁰⁾bis(tricyclohexylphosphine); palladium diacetate; sodium carbonate; potassium carbonate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; Trimethylacetic acid; In 1,4-dioxane; N,N-dimethyl-formamide; toluene; 1: Buchwald-Hartwig N-arylation;
DOI:10.1021/ol2031763