HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 2-[({9-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}methyl)amino]-N,N-diisopropylacetamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 2-amino-N,N-bis(propan-2-yl)acetamide | HCID 18348428 | — |
| Reactant | {9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}methyl methanesulfonate | HCID 59975278 | — |
| Product | 2-[({9-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}methyl)amino]-N,N-diisopropylacetamide | HCID 59975311 | 11.3% |
Reaction Steps
The title compound was prepared by a similar method to example 40 using {9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}methyl methanesulfonate (preparation 25) (374 mg, 0.66 mmol), 2-amino-N,N-diisopropylacetamide (520 mg, 3.3 mmol) (preparation 22) and N-ethyl-N-isopropyl-2-propanamine (170 mg, 1.32 mmol). The compound was purified by column chromatography on silica gel eluting with a solvent gradient of dichloromethane:methanol:ammonia (95:5:0.5) increasing in polarity to (90:10:1). The solvent was removed under reduced pressure to give a residue which was triturated with diethyl ether to give the title compound (47 mg) as a solid. MS: 632 (MH+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06326359B1 |
| Source dataset | uspto-grants-2001_12 |
| ORD ID | ord-a7654215ce2e4a19ae651f0bb3ffc60b |
| Source note | uspto-grants-2001_12 |