HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Methylpiperazine → 2-(1H-Indazol-4-yl)-6-(4-methyl-piperazin-1-ylmethyl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Methylpiperazine | HCID 53167 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | 2-(1H-Indazol-4-yl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidine-6-carbaldehyde | HCID 23650836 | — |
| Solvent | 1,2-Dichloroethane | HCID 11 | — |
| Solvent | Acetic Acid | HCID 176 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 2-(1H-Indazol-4-yl)-6-(4-methyl-piperazin-1-ylmethyl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidine | HCID 11532472 | 28.2% |
Reaction Steps
To a mixture of 2-(1H-Indazol-4-yl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidine-6-carbaldehyde (91 mg, 0.26 mmol), 1-methylpiperazine (34 mg, 0.36 mmol) and acetic acid (15 uL) in 1,2-dichloroethane (2 mL) was added sodium triacetoxyborohydride (60 mg, 0.28 mmol). The reaction mixture was stirred at room temperature overnight and then basified (NaHCO3, saturated), diluted with dichloromethane, washed with brine. Organic layer was separated, dried (MgSO4), filtered and evaporated in vacuo. The residue was purified using flash chromatography to give the title compound (33 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07872003B2 |
| Source dataset | uspto-grants-2011_01 |
| ORD ID | ord-f345d01898e842ada07e5d0268fcdf15 |
| Source note | uspto-grants-2011_01 |