HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethyl Sulfoxide → 1-Propyl-8-(1H-pyrazol-4-yl)-2-pyrrolidin-1-yl-7-(2-trimethylsilanyl-ethoxymethyl)-1,7-dihydro-purin-6-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethyl Sulfoxide | HCID 679 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | Potassium tert-butoxide | HCID 23665647 | — |
| Reactant | 8-(1-Benzyl-1H-pyrazol-4-yl)-1-propyl-2-pyrrolidin-1-yl-7-(2-trimethylsilanyl-ethoxymethyl)-1,7-dihydro-purin-6-one | HCID 67135123 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 1-Propyl-8-(1H-pyrazol-4-yl)-2-pyrrolidin-1-yl-7-(2-trimethylsilanyl-ethoxymethyl)-1,7-dihydro-purin-6-one | HCID 67135151 | 70% |
Reaction Steps
A mixture of 8-(1-Benzyl-1H-pyrazol-4-yl)-1-propyl-2-pyrrolidin-1-yl-7-(2-trimethylsilanyl-ethoxymethyl)-1,7-dihydro-purin-6-one (0.154 g, 0.29 mmol), and DMSO (0.2 ml, 2.9 mmol) was taken in THF (10 ml). 0.5M solution of KOtBu (4 ml, 2.0 mmol) in THF was added at 0° C. and stirred for 18 hours. After adding saturated NH4Cl solution, the compound was extracted with ethyl acetate (2×10 ml). Organic layer was washed with brine (2×10 ml), dried over Na2SO4. Solvent was evaporated and purified by preparative TLC to get pure 1-Propyl-8-(1H-pyrazol-4-yl)-2-pyrrolidin-1-yl-7-(2-trimethylsilanyl-ethoxymethyl)-1,7-dihydro-purin-6-one as white solid (89 mg, 70%)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08859566B2 |
| Source dataset | uspto-grants-2014_10 |
| ORD ID | ord-74e55fad7c1d402cbf5e940ed9c40b98 |
| Source note | uspto-grants-2014_10 |