Diethyl N-<4-<1-(tetrahydropyranyl-2'-oxy)-3-(2-(pivaloylamino)-3,4-dihydro-4-oxopyrido<2,3-d>pyrimidin-6-yl)prop-2-en-2-yl>benzoyl>-L-glutamate

Base Information

• Chemical Name: Diethyl N-<4-<1-(tetrahydropyranyl-2'-oxy)-3-(2-(pivaloylamino)-3,4-dihydro-4-oxopyrido<2,3-d>pyrimidin-6-yl)prop-2-en-2-yl>benzoyl>-L-glutamate
• CAS No.: 159680-66-7
• Molecular Formula: C₃₆H₄₅N₅O₉
• Molecular Weight: 691.781
• Mol file: 159680-66-7.mol

Synonyms:Diethyl N-<4-<1-(tetrahydropyranyl-2'-oxy)-3-(2-(pivaloylamino)-3,4-dihydro-4-oxopyrido<2,3-d>pyrimidin-6-yl)prop-2-en-2-yl>benzoyl>-L-glutamate

Chemical Property of Diethyl N-<4-<1-(tetrahydropyranyl-2'-oxy)-3-(2-(pivaloylamino)-3,4-dihydro-4-oxopyrido<2,3-d>pyrimidin-6-yl)prop-2-en-2-yl>benzoyl>-L-glutamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Diethyl N-<4-<1-(tetrahydropyranyl-2'-oxy)-3-(2-(pivaloylamino)-3,4-dihydro-4-oxopyrido<2,3-d>pyrimidin-6-yl)prop-2-en-2-yl>benzoyl>-L-glutamate

There total 4 articles about Diethyl N-<4-<1-(tetrahydropyranyl-2'-oxy)-3-(2-(pivaloylamino)-3,4-dihydro-4-oxopyrido<2,3-d>pyrimidin-6-yl)prop-2-en-2-yl>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: 52.0%

4-iodobenzoyl-L-glutamic acid diethyl ester (116387-21-4) + 2-(Pivaloylamino)-6-<3-(tetrahydropyranyl-2'-oxy)-cis-prop-2-en-1-yl>-4(3H)-oxopyrido<2,3-d>pyrimidine (127322-56-9) → Diethyl N-<4-<1-(tetrahydropyranyl-2'-oxy)-3-(2-(pivaloylamino)-3,4-dihydro-4-oxopyrido<2,3-d>pyrimidin-6-yl)prop-2-en-2-yl>benzoyl>-L-glutamate (159680-66-7)

Guidance literature:

With triethylamine; tris-(o-tolyl)phosphine; palladium diacetate; In acetonitrile; for 24h; Heating;

DOI:10.1021/jo00102a040

Reference yield:

3-(tetrahydropyran-2'-yloxy)propyne (6089-04-9) → Diethyl N-<4-<1-(tetrahydropyranyl-2'-oxy)-3-(2-(pivaloylamino)-3,4-dihydro-4-oxopyrido<2,3-d>pyrimidin-6-yl)prop-2-en-2-yl>benzoyl>-L-glutamate (159680-66-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 63 percent / triphenylphosphine, CuI, Et₃N / PdCl₂ / acetonitrile / 24 h / Heating

2: 87 percent / H₂ / 5percent Pd/BaSO₄, quinoline / methanol; CHCl₃ / 0.67 h

3: 52 percent / Et₃N, tris-o-tolylphosphine / Pd(OAc)2 / acetonitrile / 24 h / Heating

With copper(l) iodide; hydrogen; triethylamine; triphenylphosphine; tris-(o-tolyl)phosphine; quinoline; palladium diacetate; Pd-BaSO₄; palladium dichloride; In methanol; chloroform; acetonitrile;

DOI:10.1021/jo00102a040

Reference yield:

2-pivaloylamino-6-bromo-4(3H)-pyrido[2,3-d]pyrimidinone (116387-22-5) → Diethyl N-<4-<1-(tetrahydropyranyl-2'-oxy)-3-(2-(pivaloylamino)-3,4-dihydro-4-oxopyrido<2,3-d>pyrimidin-6-yl)prop-2-en-2-yl>benzoyl>-L-glutamate (159680-66-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 63 percent / triphenylphosphine, CuI, Et₃N / PdCl₂ / acetonitrile / 24 h / Heating

2: 87 percent / H₂ / 5percent Pd/BaSO₄, quinoline / methanol; CHCl₃ / 0.67 h

3: 52 percent / Et₃N, tris-o-tolylphosphine / Pd(OAc)2 / acetonitrile / 24 h / Heating

With copper(l) iodide; hydrogen; triethylamine; triphenylphosphine; tris-(o-tolyl)phosphine; quinoline; palladium diacetate; Pd-BaSO₄; palladium dichloride; In methanol; chloroform; acetonitrile;

DOI:10.1021/jo00102a040

upstream raw materials:

4-iodobenzoyl-L-glutamic acid diethyl ester

2-(Pivaloylamino)-6-<3-(tetrahydropyranyl-2'-oxy)-cis-prop-2-en-1-yl>-4(3H)-oxopyrido<2,3-d>pyrimidine

3-(tetrahydropyran-2'-yloxy)propyne

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

Downstream raw materials:

Diethyl N-<4-<1-hydroxy-3-(2-(pivaloylamino)-3,4-dihydro-4-oxo-5,6,7,8-tetrahydropyrido<2,3-d>pyrimidin-6-yl)prop-2-yl>benzoyl>-L-glutamate

Diethyl N-<4-<1-(tetrahydropyranyl-2'-oxy)-3-(2-(pivaloylamino)-3,4-dihydro-4-oxo-5,6,7,8-tetrahydropyrido<2,3-d>pyrimidin-6-yl)prop-2-yl>benzoyl>-L-glutamate