Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Formaldehyde | HCID 712 | — |
| Reactant | Sodium cyanoborohydride | HCID 5003444 | — |
| Reactant | HCID 59333755 | HCID 59333755 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 46198655 | HCID 46198655 | 107.6% |
Reaction Steps
2-((2-(4-(1-Methyl-1H-pyrazol-4-yl)phenylamino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)(phenyl)amino)ethanol (40 mg, 0.09 mmol) was dissolved in methanol (2 mL). Acetic acid (1.037 μL, 0.02 mmol) was added followed by formaldehyde (0.014 mL, 0.18 mmol). The reaction mixture was stirred at room temperature for 30 minutes before sodium cyanoborohydride (11.39 mg, 0.18 mmol) was added. After 20 minutes the solvent was evaporated under reduced pressure, the crude dissolved in few drops of DMF and acetonitrile, filtered and purified by preparative HPLC yielding 2-((6-methyl-2-(4-(1-methyl-1H-pyrazol-4-yl)phenylamino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)(phenyl)amino)ethanol (9.8 mg, 21%) as acetic acid salt. MS (ESI) (M+H) m/z 456;
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08188101B2 |
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| Source dataset | uspto-grants-2012_05 |
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| ORD ID | ord-edc8a28ece1042f49a09ff45f830b2a0 |
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| Source note | uspto-grants-2012_05 |
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