HuagongsheHuagongshe Chemistry Print Report · For research reference only
p-Toluenesulfonic acid monohydrate → 2-[2-Chloro-6-(4-chloro-benzyl)-pyrimidin-4-yl]-propan-2-ol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | p-Toluenesulfonic acid monohydrate | HCID 521998 | — |
| Reactant | 2-Chloro-4-(4-chloro-benzyl)-6-(1-methyl-1-trimethylsilanyloxy-ethyl)-pyrimidine | HCID 86656703 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 2-[2-Chloro-6-(4-chloro-benzyl)-pyrimidin-4-yl]-propan-2-ol | HCID 86656701 | 77% |
Reaction Steps
A solution of 2-chloro-4-(4-chloro-benzyl)-6-(1-methyl-1-trimethylsilanyloxy-ethyl)-pyrimidine (3.69 g, 10.0 mmol) and toluene-4-sulfonic acid monohydrate (0.19 g, 1.0 mmol) in 90% aqueous tetrahydrofuran (40 mL) was stirred at 20° C. for 2 h. The solution was diluted with ethyl acetate and washed successively with saturated sodium hydrogencarbonate solution and with brine. The organic layer was dried over sodium sulfate and evaporated under reduced pressure. The residual oil was crystallized from cyclohexane to give the title compound (2.28 g, 77%) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08486967B2 |
| Source dataset | uspto-grants-2013_07 |
| ORD ID | ord-6f734aee6f914c0bb343501721127eaf |
| Source note | uspto-grants-2013_07 |