HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethyl Acetate → (S)-1-(4-(benzylamino)-7-ethynylthieno[3,2-d]pyrimidin-2-ylamino)propan-2-ol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | (S)-(+)-1-Aminopropan-2-ol | HCID 7311736 | — |
| Reactant | N-benzyl-2-chloro-7-ethynylthieno[3,2-d]pyrimidin-4-amine | HCID 86675659 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | (S)-1-(4-(benzylamino)-7-ethynylthieno[3,2-d]pyrimidin-2-ylamino)propan-2-ol | HCID 53239538 | 52.3% |
Reaction Conditions
| Temperature | 120 °C |
|---|
Reaction Steps
N-Benzyl-2-chloro-7-ethynylthieno[3,2-d]pyrimidin-4-amine (30 mg, 0.096 mmol) was dissolved in anhydrous dioxane (0.5 mL) and (S)-1-aminopropan-2-ol (23 μL, 0.288 mmol) was added. The reaction mixture was stirred at 120° C. for 24 hours. After adding ethyl acetate (3 mL), the reaction mixture was washed with brine. After drying with MgSO4 and concentrating by filtration, purification by silica gel chromatography (ethyl acetate/hexane:1/3→1/1) yielded the target compound of Example 44 (17 mg, 50% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09422307B2 |
| Source dataset | uspto-grants-2016_08 |
| ORD ID | ord-9d66a8002ac840b5a63067327f44a0ea |
| Source note | uspto-grants-2016_08 |