Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetonitrile | HCID 6342 | — |
| Reactant | 7-Methoxy-1-methyl-1,2,3,4-tetrahydroisoquinolin-6-ol | HCID 46695 | — |
| Reactant | 6-Bromopyrazolo[1,5-a]pyrimidine-2-carboxylic acid | HCID 771938 | — |
| Reactant | O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate | HCID 2733207 | — |
| Product | HCID 24810832 | HCID 24810832 | 21.1% |
Reaction Steps
To a solution of 6-bromo-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid (1.4 g, 5.8 mmol, 1.0 equiv) and TBTU (2.0 g, 6.2 mmol, 1.1 equiv) in dry acetonitrile (30 mL) triethylamine (2 mL, 14.5 mmol, 2.5 equiv) is added. 7-Methoxy-1-methyl-1,2,3,4-tetrahydro-isoquinolin-6-ol (1.4 g, 7.25 mmol, 1.25 equiv) is then added. The reaction mixture is stirred at 50° C. for 2 h, then at room temperature for 8 h, and concentrated. The residue is extracted with dichloromethane. The extract is washed with water (20 ml), dried over sodium disulfate, and concentrated. The residue is purified by column chromatography on silica gel (eluent: hexane/ethyl acetate—1/1, Rf 0.3) to provide 0.511 g of the title compound as an oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07985753B2 |
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| Source dataset | uspto-grants-2011_07 |
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| ORD ID | ord-ca3a6728c09d4fdda9f7fdc37a4b36b9 |
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| Source note | uspto-grants-2011_07 |
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