diethyl N-<4-<<2-(pivaloylamino)-4-hydroxypyrido<2,3-d>pyrimidin-6-yl>ethynyl>benzoyl>-L-glutamate

Base Information

• Chemical Name: diethyl N-<4-<<2-(pivaloylamino)-4-hydroxypyrido<2,3-d>pyrimidin-6-yl>ethynyl>benzoyl>-L-glutamate
• CAS No.: 116387-24-7
• Molecular Formula: C₃₀H₃₃N₅O₇
• Molecular Weight: 575.621
• Mol file: 116387-24-7.mol

Synonyms:diethyl N-<4-<<2-(pivaloylamino)-4-hydroxypyrido<2,3-d>pyrimidin-6-yl>ethynyl>benzoyl>-L-glutamate

Chemical Property of diethyl N-<4-<<2-(pivaloylamino)-4-hydroxypyrido<2,3-d>pyrimidin-6-yl>ethynyl>benzoyl>-L-glutamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of diethyl N-<4-<<2-(pivaloylamino)-4-hydroxypyrido<2,3-d>pyrimidin-6-yl>ethynyl>benzoyl>-L-glutamate

There total 19 articles about diethyl N-<4-<<2-(pivaloylamino)-4-hydroxypyrido<2,3-d>pyrimidin-6-yl>ethynyl>benzoyl>-L-glutamate 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: 77.0%

4-iodobenzoyl-L-glutamic acid diethyl ester (116387-21-4) + 2-(pivaloylamino)-4-hydroxy-6-<(trimethylsilyl)ethynyl>pyrido<2,3-d>pyrimidine (116387-32-7) → diethyl N-<4-<<2-(pivaloylamino)-4-hydroxypyrido<2,3-d>pyrimidin-6-yl>ethynyl>benzoyl>-L-glutamate (116387-24-7)

Guidance literature:

With copper(l) iodide; triethylamine; triphenylphosphine; palladium dichloride; In acetonitrile; for 3.5h; Heating;

DOI:10.1021/jo00276a023

Reference yield: 54.0%

2-pivaloylamino-6-bromo-4(3H)-pyrido[2,3-d]pyrimidinone (116387-22-5) + diethyl N-(4-ethynylbenzoyl)-L-glutamate (116387-23-6) → diethyl N-<4-<<2-(pivaloylamino)-4-hydroxypyrido<2,3-d>pyrimidin-6-yl>ethynyl>benzoyl>-L-glutamate (116387-24-7)

Guidance literature:

With copper(l) iodide; triethylamine; triphenylphosphine; palladium dichloride; In acetonitrile; for 2.5h; Heating;

DOI:10.1021/jo00276a023

Reference yield:

tert-butyl-4-bromobenzoate (59247-47-1) → diethyl N-<4-<<2-(pivaloylamino)-4-hydroxypyrido<2,3-d>pyrimidin-6-yl>ethynyl>benzoyl>-L-glutamate (116387-24-7)

Guidance literature:

Multi-step reaction with 5 steps

1: palladium acetate, triphenylphosphine, triethylamine / 16 h / 100 °C

2: K₂CO₃ / methanol / 3 h / Ambient temperature

3: 69 percent / triphenylphosphine, triethylamine, palladium chloride, cuprous iodide / acetonitrile / 2.5 h / Heating

4: 93 percent / HCl (gas) / nitromethane / 1 h / Ambient temperature

5: 1.) N-methylmorpholine, N-methylpyrrolidone, phenyl N-phenylphosphoramidochloridate / 1.) RT, 20 min, 2.) 24 h

With 4-methyl-morpholine; 1-methyl-pyrrolidin-2-one; hydrogenchloride; copper(l) iodide; palladium diacetate; potassium carbonate; triethylamine; triphenylphosphine; Phenyl N-phenylphosphoramidochloridate; palladium dichloride; In methanol; nitromethane; acetonitrile;

DOI:10.1021/jo00276a023

upstream raw materials:

2-pivaloylamino-6-bromo-4(3H)-pyrido[2,3-d]pyrimidinone

diethyl N-(4-ethynylbenzoyl)-L-glutamate

4-iodobenzoyl-L-glutamic acid diethyl ester

2-(pivaloylamino)-4-hydroxy-6-<(trimethylsilyl)ethynyl>pyrido<2,3-d>pyrimidine

Downstream raw materials:

(6RS)-5,10-dideaza-5,6,7,8-tetrahydrofolic acid