6-[2-bromo-1-oxo-3-[2-N-[[(phenylmethoxy)carbonyl]amino][(phenylmethoxy)carbonylimino]methyl]piperidinyl]-2,4-dimethoxypyrimidine

Base Information

• Chemical Name: 6-[2-bromo-1-oxo-3-[2-N-[[(phenylmethoxy)carbonyl]amino][(phenylmethoxy)carbonylimino]methyl]piperidinyl]-2,4-dimethoxypyrimidine
• CAS No.: 214899-68-0
• Molecular Formula: C₃₁H₃₄BrN₅O₇
• Molecular Weight: 668.544

Synonyms:6-[2-bromo-1-oxo-3-[2-N-[[(phenylmethoxy)carbonyl]amino][(phenylmethoxy)carbonylimino]methyl]piperidinyl]-2,4-dimethoxypyrimidine

Chemical Property of 6-[2-bromo-1-oxo-3-[2-N-[[(phenylmethoxy)carbonyl]amino][(phenylmethoxy)carbonylimino]methyl]piperidinyl]-2,4-dimethoxypyrimidine

Chemical Property:

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Technology Process of 6-[2-bromo-1-oxo-3-[2-N-[[(phenylmethoxy)carbonyl]amino][(phenylmethoxy)carbonylimino]methyl]piperidinyl]-2,4-dimethoxypyrimidine

There total 25 articles about 6-[2-bromo-1-oxo-3-[2-N-[[(phenylmethoxy)carbonyl]amino][(phenylmethoxy)carbonylimino]methyl]piperidinyl]-2,4-dimethoxypyrimidine 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:

C15H12BrMgNO2 → 6-[2-bromo-1-oxo-3-[2-N-[[(phenylmethoxy)carbonyl]amino][(phenylmethoxy)carbonylimino]methyl]piperidinyl]-2,4-dimethoxypyrimidine (214899-68-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 62 percent / EtMgBr / tetrahydrofuran / 2 h / 0 °C

2: 92 percent / hydrogen / Pd/C / methanol; tetrahydrofuran / 20 °C

3: 74 percent / Et₃N; HgCl₂ / dimethylformamide / 2 h / 20 °C

4: 72 percent / Dess-Martin periodinane / CH₂Cl₂ / 30 h / 20 °C

5: CuBr₂ / ethyl acetate / 0.25 h / 40 °C

With ethylmagnesium bromide; hydrogen; Dess-Martin periodane; triethylamine; mercury dichloride; copper(ll) bromide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 1: Addition / 2: Hydrogenolysis / 3: Substitution / 4: Oxidation / 5: Bromination;

DOI:10.1021/ja000647j

Reference yield:

phenylmethyl 2-trimethylsilylethynyl-1(2H)-pyridinecarboxylate (214899-39-5) → 6-[2-bromo-1-oxo-3-[2-N-[[(phenylmethoxy)carbonyl]amino][(phenylmethoxy)carbonylimino]methyl]piperidinyl]-2,4-dimethoxypyrimidine (214899-68-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 97 percent / K₂CO₃ / methanol / 0.33 h / 20 °C

2: tetrahydrofuran / 0.5 h / 0 °C

3: 62 percent / EtMgBr / tetrahydrofuran / 2 h / 0 °C

4: 92 percent / hydrogen / Pd/C / methanol; tetrahydrofuran / 20 °C

5: 74 percent / Et₃N; HgCl₂ / dimethylformamide / 2 h / 20 °C

6: 72 percent / Dess-Martin periodinane / CH₂Cl₂ / 30 h / 20 °C

7: CuBr₂ / ethyl acetate / 0.25 h / 40 °C

With ethylmagnesium bromide; hydrogen; potassium carbonate; Dess-Martin periodane; triethylamine; mercury dichloride; copper(ll) bromide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 1: desilylation / 2: Substitution / 3: Addition / 4: Hydrogenolysis / 5: Substitution / 6: Oxidation / 7: Bromination;

DOI:10.1021/ja000647j

Reference yield:

phenylmethyl 2-[3-hydroxy-3-[4,6-dimethoxy-2-pyrimidinyl]-1-propynyl]-1(2H)-pyridinecarboxylate (214899-52-2) → 6-[2-bromo-1-oxo-3-[2-N-[[(phenylmethoxy)carbonyl]amino][(phenylmethoxy)carbonylimino]methyl]piperidinyl]-2,4-dimethoxypyrimidine (214899-68-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / hydrogen / Pd/C / methanol; tetrahydrofuran / 20 °C

2: 74 percent / Et₃N; HgCl₂ / dimethylformamide / 2 h / 20 °C

3: 72 percent / Dess-Martin periodinane / CH₂Cl₂ / 30 h / 20 °C

4: CuBr₂ / ethyl acetate / 0.25 h / 40 °C

With hydrogen; Dess-Martin periodane; triethylamine; mercury dichloride; copper(ll) bromide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 1: Hydrogenolysis / 2: Substitution / 3: Oxidation / 4: Bromination;

DOI:10.1021/ja000647j

upstream raw materials:

([(Z)-Benzyloxycarbonylimino]-{2-[3-(2,6-dimethoxy-pyrimidin-4-yl)-3-oxo-propyl]-piperidin-1-yl}-methyl)-carbamic acid benzyl ester

pyridine

N,N'-dibenzyloxycarbonyl-(S)-methyl-isothiourea

phenylmethyl 2-ethynyl-1(2H)-pyridinecarboxylate

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