7-(3,4-dichlorophenyl)-5-(methoxymethyl)-4,7-dihydropyrazolo[1,5-a]pyrimidine-6-carboxylic acid

Base Information

• Chemical Name: 7-(3,4-dichlorophenyl)-5-(methoxymethyl)-4,7-dihydropyrazolo[1,5-a]pyrimidine-6-carboxylic acid
• CAS No.: 343246-71-9
• Molecular Formula: C₁₅H₁₃Cl₂N₃O₃
• Molecular Weight: 354.193

Synonyms:7-(3,4-dichlorophenyl)-5-(methoxymethyl)-4,7-dihydropyrazolo[1,5-a]pyrimidine-6-carboxylic acid

Chemical Property of 7-(3,4-dichlorophenyl)-5-(methoxymethyl)-4,7-dihydropyrazolo[1,5-a]pyrimidine-6-carboxylic acid

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Technology Process of 7-(3,4-dichlorophenyl)-5-(methoxymethyl)-4,7-dihydropyrazolo[1,5-a]pyrimidine-6-carboxylic acid

There total 3 articles about 7-(3,4-dichlorophenyl)-5-(methoxymethyl)-4,7-dihydropyrazolo[1,5-a]pyrimidine-6-carboxylic acid 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: 99.0%

tert-butyl 7-(3,4-dichlorophenyl)-5-(methoxymethyl)-4,7-dihydropyrazolo[1,5-a]-pyrimidine-6-carboxylate (343246-52-6) → 7-(3,4-dichlorophenyl)-5-(methoxymethyl)-4,7-dihydropyrazolo[1,5-a]pyrimidine-6-carboxylic acid (343246-71-9)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In hexane; dichloromethane;

DOI:10.1016/j.bmcl.2009.07.083

Reference yield:

tert-butyl 4-methoxy-3-oxobutanoate (74530-59-9) → 7-(3,4-dichlorophenyl)-5-(methoxymethyl)-4,7-dihydropyrazolo[1,5-a]pyrimidine-6-carboxylic acid (343246-71-9)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydrogencarbonate / N,N-dimethyl-formamide / 24 h / 65 °C / Inert atmosphere

2: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 20 °C / Inert atmosphere

With trimethylsilyl trifluoromethanesulfonate; sodium hydrogencarbonate; In dichloromethane; N,N-dimethyl-formamide; 1: Biginelli reaction;

DOI:10.1021/jm201386u

Reference yield:

3,4-dichlorobenzaldehyde (6287-38-3) → 7-(3,4-dichlorophenyl)-5-(methoxymethyl)-4,7-dihydropyrazolo[1,5-a]pyrimidine-6-carboxylic acid (343246-71-9)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydrogencarbonate / N,N-dimethyl-formamide / 24 h / 65 °C / Inert atmosphere

2: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 20 °C / Inert atmosphere

With trimethylsilyl trifluoromethanesulfonate; sodium hydrogencarbonate; In dichloromethane; N,N-dimethyl-formamide; 1: Biginelli reaction;

DOI:10.1021/jm201386u

upstream raw materials:

tert-butyl 7-(3,4-dichlorophenyl)-5-(methoxymethyl)-4,7-dihydropyrazolo[1,5-a]-pyrimidine-6-carboxylate

tert-butyl 4-methoxy-3-oxobutanoate

3,4-dichlorobenzaldehyde

Downstream raw materials:

((R)-7-(3,4-dichlorophenyl)-5-(methoxymethyl)-4,7-dihydropyrazolo[1,5-a]pyrimidin-6-yl)((S)-2-(3-methylisoxazol-5-yl)pyrrolidin-1-yl)methanone

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