HuagongsheHuagongshe Chemistry Print Report · For research reference only
(2-Aminopyrimidin-5-yl)boronic acid → 3-(2-(2-aminopyrimidin-5-yl)-8-(2-hydroxypropan-2-yl)-6-morpholino-9H-purin-9-yl)propan-1-ol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | (2-Aminopyrimidin-5-yl)boronic acid | HCID 17750211 | — |
| Reactant | 2-(9-(3-(tert-butyldimethylsilyloxy)propyl)-2-chloro-6-morpholino-9H-purin-8-yl)propan-2-ol | HCID 86637237 | — |
| Reactant | HCID 178458928 | HCID 178458928 | — |
| Product | 3-(2-(2-aminopyrimidin-5-yl)-8-(2-hydroxypropan-2-yl)-6-morpholino-9H-purin-9-yl)propan-1-ol | HCID 44545042 | — |
Reaction Steps
100 mg of 2-(2-chloro-6-morpholino-9H-purin-8-yl)propan-2-ol was treated with TBDMS-protected bromopropanol via General Procedure C. Crude intermediate 2-(9-(3-(tert-butyldimethylsilyloxy)propyl)-2-chloro-6-morpholino-9H-purin-8-yl)propan-2-ol was treated with 2-aminopyrimidine-5-boronic acid, pinacol ester via General Procedure A and was purified via reverse phase HPLC to give 36 mg of 105 as a white solid. MS (Q1) 415.2 (M)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08158624B2 |
| Source dataset | uspto-grants-2012_04 |
| ORD ID | ord-a86fb37255b742af8a7364abbdd1d0b3 |
| Source note | uspto-grants-2012_04 |