HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 5-Bromo-2-(methylthio)pyrimidine-4-carbaldehyde
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | Aluminium lithium hydride | HCID 21226445 | — |
| Reactant | 5-bromo-N-methoxy-N-methyl-2-(methylthio)pyrimidine-4-carboxamide | HCID 90280334 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 5-Bromo-2-(methylthio)pyrimidine-4-carbaldehyde | HCID 54271495 | — |
Reaction Steps
A solution of 5-bromo-N-methoxy-N-methyl-2-(methylthio)pyrimidine-4-carboxamide (11A, 8.2 g, 28 mmol) in THF (120 mL) was added dropwise to a suspension of lithium aluminum hydride (1.06 G, 28 mmol) and THF (120 mL) at −78° C. The mixture was stirred for 10 minutes after addition finish. H2O (1.06 mL), 15% aqueous NaOH solution (1.06 mL) and H2O (3.18 mL) were successively added to the mixture at 0° C. very slowly. The resulting precipitate was filtered and washed with THF. The filtrate was concentrated in vacuo to afford crude of the title compound. MS (m/z): 233.14, [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09050344B2 |
| Source dataset | uspto-grants-2015_06 |
| ORD ID | ord-56e05154f5b4483a8c1a60f055d18f8e |
| Source note | uspto-grants-2015_06 |