Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Thiophenol | HCID 7969 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 6-Chloro-2-fluoropurine | HCID 5287914 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 11230343 | HCID 11230343 | 83% |
Reaction Steps
To a solution of 2-fluoro-6-chloropurine (10.0 g, 57.9 mmol) in methanol (200 mL) is added diisopropylethylamine (25.2 mL, 144.7 mmol). The mixture is cooled to 0° C. and followed by slow addition of thiophenol (11.9 mL, 115.8 mmol) via an addition funnel over one hour. The reaction is stirred at 0° C. for 12 hours. The solvent is then removed under reduced pressure and the solid is collected by filtration and washed twice with hexanes. The collected solid is further purified by re-crystallization from methanol to afford desired product (11.8 g, 83% yield). 1H NMR (400 MHz, (CD3)2SO) δ 7.54 (m, 3H), 7.66(m, 2H), 8.49(s, 1H); MS C11H7FN4S [MH+] 246.04, found: 247.05.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06949644B2 |
|---|
| Source dataset | uspto-grants-2005_09 |
|---|
| ORD ID | ord-cb69779fba3a4be49e56b2e09dfa4b7a |
|---|
| Source note | uspto-grants-2005_09 |
|---|