HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ammonia → (S)-1-(3-Hydroxy-4-(4-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)phenyl)urea
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ammonia | HCID 222 | — |
| Reactant | Boron tribromide | HCID 25134 | — |
| Reactant | (S)-1-(3-Methoxy-4-(4-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)phenyl)urea | HCID 131736234 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (S)-1-(3-Hydroxy-4-(4-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)phenyl)urea | HCID 73776069 | 12% |
Reaction Steps
(S)-1-(3-Methoxy-4-(4-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)phenyl)urea (34 mg, 0.05 mmol) was treated with boron tribromide (1M in dichloromethane, 1.5 mL, 1.5 mmol) in dichloromethane (1.0 mL) and then with a solution of ammonia (7N in methanol, 5.0 mL, 35.0 mmol) according to the method described in Example 41. The residue was purified using SP1® Purification System (0% to 10% dichloromethane-methanol) to obtain 3 mg (12% yield) of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09388189B2 |
| Source dataset | uspto-grants-2016_07 |
| ORD ID | ord-7901a792e640495bbf7c959bf88b58ec |
| Source note | uspto-grants-2016_07 |