HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → Tert-butyl 6-(methoxymethyl)pyrimidin-4-ylcarbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | 4-Chloro-6-(methoxymethyl)pyrimidine | HCID 14306171 | — |
| Reactant | Tert-butylcarbamate | HCID 21252905 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | Tert-butyl 6-(methoxymethyl)pyrimidin-4-ylcarbamate | HCID 21934671 | — |
Reaction Steps
To a solution of 4-chloro-6-(methoxymethyl)pyrimidine (768 mg, 4.84 mmole) in dry dioxane (10 mL) was added Cs2CO3 (2.37 g, 7.26 mmole), Xanthphos (84 mg, 0.15 mmole), Pd2(dba)3 (44 mg, 0.05 mmole), and tert-butylcarbamate (681 mg, 5.81 mmole) then the mixture was heated to reflux. After 3 hours, the mixture was cooled to room temperature, diluted with H2O, and extracted with CH2Cl2 (3×). The combined organic layers were dried (MgSO4), filtered, and concentrated. Flash column chromatography (35% EtOAc/hexanes) gave the title compound as a pale yellow solid. 1H-NMR (500 MHz, CDCl3) δ 8.74 (s, 1H), 8.04 (s, 1H), 8.00 (bs, 1H), 4.51 (s, 2H), 3.51 (s, 3H), 1.55 (s, 9H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07115597B2 |
| Source dataset | uspto-grants-2006_10 |
| ORD ID | ord-094a03491c6d47d49c0b03c1f6d3f794 |
| Source note | uspto-grants-2006_10 |