4-[5-(tert-butyl-diphenyl-silanyloxymethyl)-4-chloro-2-methyl-6,7-dihydro-5H-pyrido[2,3-d]pyrimidin-8-yl]-3-methyl-benzonitrile

Base Information

Chemical Name:4-[5-(tert-butyl-diphenyl-silanyloxymethyl)-4-chloro-2-methyl-6,7-dihydro-5H-pyrido[2,3-d]pyrimidin-8-yl]-3-methyl-benzonitrile
CAS No.:476645-16-6
Molecular Formula:C₃₃H₃₅ClN₄OSi
Molecular Weight:567.206
Hs Code.:

4-[5-(<i>tert</i>-butyl-diphenyl-silanyloxymethyl)-4-chloro-2-methyl-6,7-dihydro-5<i>H</i>-pyrido[2,3-<i>d</i>]pyrimidin-8-yl]-3-methyl-benzonitrile

Synonyms:4-[5-(tert-butyl-diphenyl-silanyloxymethyl)-4-chloro-2-methyl-6,7-dihydro-5H-pyrido[2,3-d]pyrimidin-8-yl]-3-methyl-benzonitrile

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Chemical Property of 4-[5-(tert-butyl-diphenyl-silanyloxymethyl)-4-chloro-2-methyl-6,7-dihydro-5H-pyrido[2,3-d]pyrimidin-8-yl]-3-methyl-benzonitrile

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Technology Process of 4-[5-(tert-butyl-diphenyl-silanyloxymethyl)-4-chloro-2-methyl-6,7-dihydro-5H-pyrido[2,3-d]pyrimidin-8-yl]-3-methyl-benzonitrile

There total 11 articles about 4-[5-(tert-butyl-diphenyl-silanyloxymethyl)-4-chloro-2-methyl-6,7-dihydro-5H-pyrido[2,3-d]pyrimidin-8-yl]-3-methyl-benzonitrile 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: 48.0%

: methanesulfonic acid 4-(tert-butyl-diphenyl-silanyloxy)-3-[4-chloro-6-(4-cyano-2-methyl-phenylamino)-2-methyl-pyrimidin-5-yl]-butyl ester

: 476645-16-6
4-[5-(tert-butyl-diphenyl-silanyloxymethyl)-4-chloro-2-methyl-6,7-dihydro-5H-pyrido[2,3-d]pyrimidin-8-yl]-3-methyl-benzonitrile

Guidance literature:: With triethylamine; In tetrahydrofuran; at 0 - 20 ℃; for 16h;
DOI:10.1016/j.bmcl.2005.05.040

Reference yield:

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

: 476645-16-6
4-[5-(tert-butyl-diphenyl-silanyloxymethyl)-4-chloro-2-methyl-6,7-dihydro-5H-pyrido[2,3-d]pyrimidin-8-yl]-3-methyl-benzonitrile

Guidance literature:: Multi-step reaction with 10 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 / CH₂Cl₂ / 3 h / 20 °C

8.1: Et₃N / CH₂Cl₂ / 18 h / 20 °C

9.1: TFA / CH₂Cl₂ / 18 h / 20 °C

10.1: 48 percent / Et₃N / tetrahydrofuran / 16 h / 0 - 20 °C

With 1H-imidazole; dmap; sodium hydride; diisobutylaluminium hydride; ozone; triethylamine; trifluoroacetic acid; lithium hexamethyldisilazane; trichlorophosphate; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.bmcl.2005.05.040

Reference yield:

: 474103-23-6
2-(4,6-dichloro-2-methyl-pyrimidin-5-yl)-pent-4-en-1-ol

: 476645-16-6
4-[5-(tert-butyl-diphenyl-silanyloxymethyl)-4-chloro-2-methyl-6,7-dihydro-5H-pyrido[2,3-d]pyrimidin-8-yl]-3-methyl-benzonitrile

Guidance literature:: Multi-step reaction with 7 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 / CH₂Cl₂ / 3 h / 20 °C

5.1: Et₃N / CH₂Cl₂ / 18 h / 20 °C

6.1: TFA / CH₂Cl₂ / 18 h / 20 °C

7.1: 48 percent / Et₃N / tetrahydrofuran / 16 h / 0 - 20 °C

With 1H-imidazole; dmap; sodium hydride; ozone; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.bmcl.2005.05.040