Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Potassium Cyanide | HCID 9032 | — |
| Reactant | Cyanogen Bromide | HCID 10476 | — |
| Reactant | 18-Crown-6 | HCID 28557 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | HCID 178430501 | HCID 178430501 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 86608508 | HCID 86608508 | — |
Reaction Steps
A solution of KCN (325.6 mg, 5.0 mmol) in 5% strength NaHCO3 solution (7 ml) was added to 484.6 mg (1.0 mmol) of 1-(4-{4-[2-tert-butyl-6-(trifluoromethyl)pyrimidin-4-yl]piperazin-1-yl}butyl)-4-mercapto-5-methylpyrimidin-2(1H)-one from Example 2 in 20 ml of methylene chloride. Then a mixture of 2.0 mg of 18-crown-6 and 105.9 mg (1.0 mmol) of BrCN, in the minimum amount of methylene chloride necessary to dissolve, was added dropwise at 0° C. The organic phase was then separated off and washed twice with saturated aqueous brine. The organic phase was dried over Na2SO4 and filtered to remove the desiccant, and the solvent was evaporated to dryness in vacuo; yield: 420.0 mg. 1-(4-{4-[2-tert-Butyl-6-(trifluoromethyl)pyrimidin-4-yl]piperazin-1-yl}butyl)-5-methyl-2-oxo-1,2-dihydropyrimidin-4-yl thiocyanate was employed without additional purification in the next step.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08008488B2 |
|---|
| Source dataset | uspto-grants-2011_08 |
|---|
| ORD ID | ord-80631159f2294adc92a06fe4cdb0d105 |
|---|
| Source note | uspto-grants-2011_08 |
|---|