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

Base Information

• Chemical Name: [8-(2,4-bis-trifluoromethyl-phenyl)-4-chloro-2-methyl-5,6,7,8-tetrahydro-pyrido[2,3-d]pyrimidin-5-yl]-methanol
• CAS No.: 474103-60-1
• Molecular Formula: C₁₇H₁₄ClF₆N₃O
• Molecular Weight: 425.761
• Mol file: 474103-60-1.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 12 articles about [8-(2,4-bis-trifluoromethyl-phenyl)-4-chloro-2-methyl-5,6,7,8-tetrahydro-pyrido[2,3-d]pyrimidin-5-yl]-methanol 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)-5-(tert-butyl-diphenyl-silanyloxymethyl)-4-chloro-2-methyl-5,6,7,8-tetrahydro-pyrido[2,3-d]pyrimidine (474103-59-8) → [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)

Guidance literature:

With triethylamine tris(hydrogen fluoride); In N,N-dimethyl-formamide; at 40 ℃; for 4h;

DOI:10.1016/j.bmcl.2005.05.040

Reference yield:

(4,6-dihydroxy-2-methyl-pyrimidin-5-yl)-acetic acid ethyl ester → [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)

Guidance literature:

Multi-step reaction with 11 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

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) → [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)

Guidance literature:

Multi-step reaction with 8 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

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)-5-(tert-butyl-diphenyl-silanyloxymethyl)-4-chloro-2-methyl-5,6,7,8-tetrahydro-pyrido[2,3-d]pyrimidine

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

(2,4-bis-trifluoromethyl-phenyl)-{5-[1-(tert-butyl-diphenyl-silanyloxymethyl)-but-3-enyl]-6-chloro-2-methyl-pyrimidin-4-yl}-amine

Downstream raw materials:

5-(2,4-bis-trifluoromethyl-phenyl)-7-methyl-1-(1-propyl-butyl)-1,2,2a,3,4,5-hexahydro-1,5,6,8-tetraaza-acenaphthylene

5-(2,4-bis-trifluoromethyl-phenyl)-1-(1-ethyl-propyl)-7-methyl-1,2,2a,3,4,5-hexahydro-1,5,6,8-tetraaza-acenaphthylene

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

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