(S)-2-Acetoxy-propionic acid (S)-8-(2,4-bis-trifluoromethyl-phenyl)-4-chloro-2-methyl-5,6,7,8-tetrahydro-pyrido[2,3-d]pyrimidin-5-ylmethyl ester

Base Information

• Chemical Name: (S)-2-Acetoxy-propionic acid (S)-8-(2,4-bis-trifluoromethyl-phenyl)-4-chloro-2-methyl-5,6,7,8-tetrahydro-pyrido[2,3-d]pyrimidin-5-ylmethyl ester
• CAS No.: 474103-65-6
• Molecular Formula: C₂₂H₂₀ClF₆N₃O₄
• Molecular Weight: 539.862
• Mol file: 474103-65-6.mol

Synonyms:(S)-2-Acetoxy-propionic acid (S)-8-(2,4-bis-trifluoromethyl-phenyl)-4-chloro-2-methyl-5,6,7,8-tetrahydro-pyrido[2,3-d]pyrimidin-5-ylmethyl ester

Chemical Property of (S)-2-Acetoxy-propionic acid (S)-8-(2,4-bis-trifluoromethyl-phenyl)-4-chloro-2-methyl-5,6,7,8-tetrahydro-pyrido[2,3-d]pyrimidin-5-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-Acetoxy-propionic acid (S)-8-(2,4-bis-trifluoromethyl-phenyl)-4-chloro-2-methyl-5,6,7,8-tetrahydro-pyrido[2,3-d]pyrimidin-5-ylmethyl ester

There total 13 articles about (S)-2-Acetoxy-propionic acid (S)-8-(2,4-bis-trifluoromethyl-phenyl)-4-chloro-2-methyl-5,6,7,8-tetrahydro-pyrido[2,3-d]pyrimidin-5-ylmethyl ester 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:

[8-(2,4-bis-trifluoromethyl-phenyl)-4-chloro-2-methyl-5,6,7,8-tetrahydro-pyrido[2,3-d]pyrimidin-5-yl]-methanol (474103-60-1) + (S)-2-acetoxypropanoyl chloride (36394-75-9) → (S)-2-Acetoxy-propionic acid (R)-8-(2,4-bis-trifluoromethyl-phenyl)-4-chloro-2-methyl-5,6,7,8-tetrahydro-pyrido[2,3-d]pyrimidin-5-ylmethyl ester (474103-66-7) + (S)-2-Acetoxy-propionic acid (S)-8-(2,4-bis-trifluoromethyl-phenyl)-4-chloro-2-methyl-5,6,7,8-tetrahydro-pyrido[2,3-d]pyrimidin-5-ylmethyl ester (474103-65-6)

Guidance literature:

With dmap; In dichloromethane; at 0 ℃; for 0.5h;

DOI:10.1016/j.bmcl.2005.05.040

Reference yield:

(4,6-dihydroxy-2-methyl-pyrimidin-5-yl)-acetic acid ethyl ester → (S)-2-Acetoxy-propionic acid (S)-8-(2,4-bis-trifluoromethyl-phenyl)-4-chloro-2-methyl-5,6,7,8-tetrahydro-pyrido[2,3-d]pyrimidin-5-ylmethyl ester (474103-65-6)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 73 percent / POCl₃ / 3.5 h / Heating

2.1: 68 percent / LiHMDS / hexane; tetrahydrofuran / 0 - 20 °C

3.1: 86 percent / DIBAl-H / hexane; CH₂Cl₂ / 3 h / -78 - 0 °C

4.1: 90 percent / imidazole; DMAP / dimethylformamide / 2 h / 0 - 20 °C

5.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

5.2: tetrahydrofuran / 5 h / Heating

6.1: DMAP / CH₂Cl₂ / 48 h / 20 °C

7.1: O₃ / CH₂Cl₂ / 0.5 h / -78 °C

7.2: NaBH₄ / 3 h / 20 °C

8.1: Et₃N / CH₂Cl₂ / 18 h / 20 °C

9.1: TFA / CH₂Cl₂ / 18 h / 20 °C

10.1: Et₃N / tetrahydrofuran / 16 h / 0 - 20 °C

11.1: Et₃N*3HF / dimethylformamide / 4 h / 40 °C

12.1: DMAP / CH₂Cl₂ / 0.5 h / 0 °C

With 1H-imidazole; dmap; sodium hydride; diisobutylaluminium hydride; ozone; triethylamine tris(hydrogen fluoride); triethylamine; trifluoroacetic acid; lithium hexamethyldisilazane; trichlorophosphate; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2005.05.040

Reference yield:

2-(4,6-dichloro-2-methyl-pyrimidin-5-yl)-pent-4-en-1-ol (474103-23-6) → (S)-2-Acetoxy-propionic acid (S)-8-(2,4-bis-trifluoromethyl-phenyl)-4-chloro-2-methyl-5,6,7,8-tetrahydro-pyrido[2,3-d]pyrimidin-5-ylmethyl ester (474103-65-6)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 90 percent / imidazole; DMAP / dimethylformamide / 2 h / 0 - 20 °C

2.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

2.2: tetrahydrofuran / 5 h / Heating

3.1: DMAP / CH₂Cl₂ / 48 h / 20 °C

4.1: O₃ / CH₂Cl₂ / 0.5 h / -78 °C

4.2: NaBH₄ / 3 h / 20 °C

5.1: Et₃N / CH₂Cl₂ / 18 h / 20 °C

6.1: TFA / CH₂Cl₂ / 18 h / 20 °C

7.1: Et₃N / tetrahydrofuran / 16 h / 0 - 20 °C

8.1: Et₃N*3HF / dimethylformamide / 4 h / 40 °C

9.1: DMAP / CH₂Cl₂ / 0.5 h / 0 °C

With 1H-imidazole; dmap; sodium hydride; ozone; triethylamine tris(hydrogen fluoride); triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2005.05.040

upstream raw materials:

[8-(2,4-bis-trifluoromethyl-phenyl)-4-chloro-2-methyl-5,6,7,8-tetrahydro-pyrido[2,3-d]pyrimidin-5-yl]-methanol

(S)-2-acetoxypropanoyl chloride

2-(4,6-dichloro-2-methyl-pyrimidin-5-yl)-pent-4-en-1-ol

5-[1-(tert-butyl-diphenyl-silanyloxymethyl)-but-3-enyl]-4,6-dichloro-2-methyl-pyrimidine

Downstream raw materials:

[8-(2,4-bis-trifluoromethyl-phenyl)-4-chloro-2-methyl-5,6,7,8-tetrahydro-pyrido[2,3-d]pyrimidin-5-yl]-methanol

methanesulfonic acid 8-(2,4-bis-trifluoromethyl-phenyl)-4-chloro-2-methyl-5,6,7,8-tetrahydro-pyrido[2,3-d]pyrimidin-5-ylmethyl ester