HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethyl chloroformate → (S)-ethyl 2-(4-(3-cyclopropylureido)phenyl)-4-(3-methylmorpholino)-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethyl chloroformate | HCID 10928 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | (S)-1-cyclopropyl-3-(4-(4-(3-methylmorpholino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-yl)phenyl)urea | HCID 46894114 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | (S)-ethyl 2-(4-(3-cyclopropylureido)phenyl)-4-(3-methylmorpholino)-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylate | HCID 46912384 | — |
Reaction Steps
To a solution of (S)-1-cyclopropyl-3-(4-(4-(3-methylmorpholino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-yl)phenyl)urea (example 3) (50 mg 0.13 mmol) in dioxane (3 mL) at room temperature (20° C.) was added sodium hydrogencarbonate (22 mg 0.26 mmol) followed by ethyl chloroformate (14 uL 0.15 mmol). The reaction mixture was stirred for 16 h. The solvent was removed in vacuo and the residue partitioned between DCM and water. The organic phase was passed through a 1 micron PTFE filter to dry and then evaporated in vacuo to afford (38 mg 64%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08785457B2 |
| Source dataset | uspto-grants-2014_07 |
| ORD ID | ord-7075027403cb4a1c8f4df49ab2b87a36 |
| Source note | uspto-grants-2014_07 |