HuagongsheHuagongshe Chemistry Print Report · For research reference only
Carbonate Ion → 6-[(cyclopropylmethyl)(propyl)amino]-N-{2-methyl-4-[(2-oxopyrrolidin-1-yl)methyl]phenyl}pyrimidine-4-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Carbonate Ion | HCID 19660 | — |
| Reactant | Triacetoxyborohydride | HCID 2724942 | — |
| Reactant | Tert-butyl 4-aminobutanoate hydrochloride | HCID 24750478 | — |
| Reactant | HCID 59446872 | HCID 59446872 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 6-[(cyclopropylmethyl)(propyl)amino]-N-{2-methyl-4-[(2-oxopyrrolidin-1-yl)methyl]phenyl}pyrimidine-4-carboxamide | HCID 25183066 | 72% |
Reaction Steps
A solution of 6-((cyclopropylmethyl)(propyl)amino)-N-(4-formyl-2-methylphenyl)pyrimidine-4-carboxamide (Intermediate 29, 100 mg; 0.28 mmol) in DCM (5 ml) was treated with tert-butyl 4-aminobutanoate hydrochloride (Bachem, 244.6 mg; 1.25 mmol) and polymer supported carbonate (150 mg) followed by polymer supported triacetoxy borohydride (150 mg). After stirring for 18 hours the mixture was filtered and the solvent removed in vacuo. The residue was purified by column chromatography (silica) eluting with petroleum ether containing increasing amounts of EtOAc to give the title compound as a white solid (85 mg, 70%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09150519B2 |
| Source dataset | uspto-grants-2015_10 |
| ORD ID | ord-86b12a104efc4fac9be243a4362cff92 |
| Source note | uspto-grants-2015_10 |