Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | Oxane-3-carbaldehyde | HCID 10129928 | — |
| Reactant | 9-(3-Aminopropyl)-2-butoxy-8-methoxy-9H-purin-6-amine | HCID 23158546 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 67212082 | HCID 67212082 | 70.4% |
Reaction Steps
Tetrahydro-2H-pyran-3-carbaldehyde (19.39 mg, 0.17 mmol) was added to 9-(3-aminopropyl)-2-(butyloxy)-8-(methyloxy)-9H-purin-6-amine (50 mg, 0.17 mmol) in DCM (1 ml). Sodium triacetoxyborohydride (72.0 mg, 0.34 mmol) and DCM (1 ml) was added followed by acetic acid (0.024 ml, 0.425 mmol). The mixture was stirred at 20° C. under nitrogen for 5 hours. The mixture was quenched with NaHCO3 (5 ml) and diluted with DCM (2 ml). The organic layer was separated using a hydrophobic frit and the solvent removed in vacuo. The sample was dissolved in 1:1 MeOH:DMSO (1 ml) and purified by Mass Directed AutoPrep (Method A). The solvent was dried under a stream of nitrogen to give the title compound as white solid (47 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08575181B2 |
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| Source dataset | uspto-grants-2013_11 |
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| ORD ID | ord-f97c761cdf204445a8c0c0141f8779d6 |
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| Source note | uspto-grants-2013_11 |
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