Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | L-Proline | HCID 145742 | — |
| Reactant | Sodium methanesulfinate | HCID 2733271 | — |
| Reactant | HCID 58233690 | HCID 58233690 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | HCID 58233702 | HCID 58233702 | 12.1% |
Reaction Steps
Copper (I) iodide (28 mg, 0.15 mmol, 0.4 eq) was added to a degassed solution of 7-bromospiro[chromeno[3,4-d]pyrimidine-5,1′-cyclohexan]-3-amine (44) (0.126 g, 0.36 mmol), (S)-pyrrolidine-2-carboxylic acid (0.034 g, 0.29 mmol), sodium methanesulfinate (0.074 g, 0.73 mmol) and sodium hydroxide (0.015 g, 0.36 mmol) in DMSO (1 mL) under Argon. The mixture was heated at 100° C., for 4 days. After workup, chromatography on silica gel afforded 15 mg of 7-(methylsulfonyl)spiro[chromeno[3,4-d]pyrimidine-5,1′-cyclohexan]-3-amine (45) as a brown solid. LCMS-ESI (POS), M/Z, M+1: Found 345.9.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08389533B2 |
|---|
| Source dataset | uspto-grants-2013_03 |
|---|
| ORD ID | ord-614226dfee88497295acece3c37bf77a |
|---|
| Source note | uspto-grants-2013_03 |
|---|
