HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → (2R)-2-{2-Chloro-5-[2-chloro-7-((1R)-1-hydroxymethylbutylamino)-thiazolo[4,5-d]pyrimidin-5-yldisulfanyl]-thiazolo[4,5-d]pyrimidin-7-ylamino}-pentan-1-ol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Sodium Nitrite | HCID 23668193 | — |
| Reactant | HCID 178448295 | HCID 178448295 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | (2R)-2-{2-Chloro-5-[2-chloro-7-((1R)-1-hydroxymethylbutylamino)-thiazolo[4,5-d]pyrimidin-5-yldisulfanyl]-thiazolo[4,5-d]pyrimidin-7-ylamino}-pentan-1-ol | HCID 86625795 | 78% |
Reaction Steps
(2R)-2-[(2-Amino-5-mercapto[1,3]thiazolo[4,5-d]pyrimidin-7-yl)amino]pentan-1-ol (4.0 g, 14 mmol) was dissolved in acetonitrile (100 ml) and concentrated hydrochloric acid (150 mL). Sodium nitrite (1.93 g, 28 mmol) was dissolved in water (10 mL) and added at 0° C. The reaction mixture was left at 0° C. for 2 days until the reaction was complete by LCMS. The reaction mixture was poured onto ice and the precipitated product was collected by filtration. The solid was dried in vacuo to give 3.3 g (78% yield) of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07960395B2 |
| Source dataset | uspto-grants-2011_06 |
| ORD ID | ord-d2e50841e782430bad3149d05bfba6a6 |
| Source note | uspto-grants-2011_06 |