1-(2,6-difluoro-benzyl)-5-(3-methoxy-phenyl)-6-methyl-3-[2-(2-pyridin-2-yl-ethylamino)-propyl]-1H-pyrimidine-2,4-dione

Base Information

• Chemical Name: 1-(2,6-difluoro-benzyl)-5-(3-methoxy-phenyl)-6-methyl-3-[2-(2-pyridin-2-yl-ethylamino)-propyl]-1H-pyrimidine-2,4-dione
• CAS No.: 352298-75-0
• Molecular Formula: C₂₉H₃₀F₂N₄O₃
• Molecular Weight: 520.579

Synonyms:1-(2,6-difluoro-benzyl)-5-(3-methoxy-phenyl)-6-methyl-3-[2-(2-pyridin-2-yl-ethylamino)-propyl]-1H-pyrimidine-2,4-dione

Chemical Property of 1-(2,6-difluoro-benzyl)-5-(3-methoxy-phenyl)-6-methyl-3-[2-(2-pyridin-2-yl-ethylamino)-propyl]-1H-pyrimidine-2,4-dione

Chemical Property:

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Technology Process of 1-(2,6-difluoro-benzyl)-5-(3-methoxy-phenyl)-6-methyl-3-[2-(2-pyridin-2-yl-ethylamino)-propyl]-1H-pyrimidine-2,4-dione

There total 7 articles about 1-(2,6-difluoro-benzyl)-5-(3-methoxy-phenyl)-6-methyl-3-[2-(2-pyridin-2-yl-ethylamino)-propyl]-1H-pyrimidine-2,4-dione 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:

2‐(pyridin‐2‐yl)acetaldehyde (54765-14-9) + 3-(2-amino-propyl)-1-(2,6-difluoro-benzyl)-5-(3-methoxy-phenyl)-6-methyl-1H-pyrimidine-2,4-dione (352290-54-1) → 1-(2,6-difluoro-benzyl)-5-(3-methoxy-phenyl)-6-methyl-3-[2-(2-pyridin-2-yl-ethylamino)-propyl]-1H-pyrimidine-2,4-dione (352298-75-0)

Guidance literature:

With sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane;

DOI:10.1016/S0960-894X(03)00620-6

Reference yield:

N-(2,6-difluorobenzyl) urea (17751-24-5) → 1-(2,6-difluoro-benzyl)-5-(3-methoxy-phenyl)-6-methyl-3-[2-(2-pyridin-2-yl-ethylamino)-propyl]-1H-pyrimidine-2,4-dione (352298-75-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 60 percent / pyridine / 24 h / 20 °C

2.1: 94 percent / AcOH / 1 h / Heating

3.1: 88 percent / Br₂; AcOH / 1 h / 20 °C

4.1: 94.2 percent / PPh₃; di-tert-butylazodicarboxylate / tetrahydrofuran / 16 h / 20 °C

5.1: Pd(PPh₃)4; aq. Na₂CO₃ / toluene / Heating

6.1: TFA / CH₂Cl₂

7.1: 1,2-dichloro-ethane / 0.17 h

7.2: NaBH(OAc)3 / 1,2-dichloro-ethane / 10 h / 20 °C

With pyridine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; di-tert-butyl-diazodicarboxylate; bromine; sodium carbonate; acetic acid; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; toluene; 4.1: Mitsunobu reaction / 5.1: Suzuki coupling;

DOI:10.1021/jm030472z

Reference yield:

2,6-difluorobenzylamine (69385-30-4) → 1-(2,6-difluoro-benzyl)-5-(3-methoxy-phenyl)-6-methyl-3-[2-(2-pyridin-2-yl-ethylamino)-propyl]-1H-pyrimidine-2,4-dione (352298-75-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 79 percent / aq. HCl / Heating

2.1: 60 percent / pyridine / 24 h / 20 °C

3.1: 94 percent / AcOH / 1 h / Heating

4.1: 88 percent / Br₂; AcOH / 1 h / 20 °C

5.1: 94.2 percent / PPh₃; di-tert-butylazodicarboxylate / tetrahydrofuran / 16 h / 20 °C

6.1: Pd(PPh₃)4; aq. Na₂CO₃ / toluene / Heating

7.1: TFA / CH₂Cl₂

8.1: 1,2-dichloro-ethane / 0.17 h

8.2: NaBH(OAc)3 / 1,2-dichloro-ethane / 10 h / 20 °C

With pyridine; hydrogenchloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; di-tert-butyl-diazodicarboxylate; bromine; sodium carbonate; acetic acid; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; toluene; 5.1: Mitsunobu reaction / 6.1: Suzuki coupling;

DOI:10.1021/jm030472z

upstream raw materials:

2‐(pyridin‐2‐yl)acetaldehyde

3-(2-amino-propyl)-1-(2,6-difluoro-benzyl)-5-(3-methoxy-phenyl)-6-methyl-1H-pyrimidine-2,4-dione

2,6-difluorobenzylamine

N-(2,6-difluorobenzyl) urea

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