HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,3-Propanediol → 3-({6-Chloro-2-[(2,3-difluorobenzyl)thio]pyrimidin-4-yl}oxy)propan-1-ol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,3-Propanediol | HCID 10442 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | N-[2-[[(2,3-difluorophenyl)methyl]thio]-6-[2-hydroxy-1-(hydroxymethyl)ethoxy]-4-pyrimidinyl]-1-azetidinesulfonamide | HCID 11698344 | — |
| Reactant | 4,6-Dichloro-2-((2,3-difluorobenzyl)thio)pyrimidine | HCID 85928037 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 3-({6-Chloro-2-[(2,3-difluorobenzyl)thio]pyrimidin-4-yl}oxy)propan-1-ol | HCID 86619894 | — |
Reaction Steps
To a solution of 4,6-dichloro-2-[(2,3-difluorobenzyl)thio]pyrimidine (the product of example 1 step 3 g) and propane-1,3-diol (1.1 g) in THF (50 ml) was added NaH (390 mg) slowly and the reaction was then allowed to stir at room temperature for 18 h. The reaction mixture was then partitioned between DCM (150 ml) and H2O (100 ml). The organics were separated and the aqueous layer was re-extracted with DCM (2×150 ml). Organics were combined, dried (MgSO4) and reduced in vacuo to give the subtitle compound as a yellow oil. Yield 2.9 g
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08269002B2 |
| Source dataset | uspto-grants-2012_09 |
| ORD ID | ord-b6d0620b155849ccbf12d44b5dcb7001 |
| Source note | uspto-grants-2012_09 |