Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Diethyl Ether | HCID 3283 | — |
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Reactant | HCID 21073791 | HCID 21073791 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 21073794 | HCID 21073794 | 45.7% |
Reaction Steps
To a solution of 7-[4-(4-chroman-8-yl-piperazin-1-yl)-butoxy]-1H-pyrido[2,3-d]pyrimidin-2-one (320 mg) in THF (6 mL) and MeOH (2 mL) was added NaBH4 (54 mg) in portions. After the addition was over, the mixture was kept stirring overnight. The reaction was quenched with H2O. The mixture was extracted with CH2Cl2 (3×50 mL). The combined organic phases were dried over Na2SO4 and concentrated. The residue was purified by chromatography on silica gel to give a semi-solid which was converted to its HCl salt by treating with 1 equivalent of 1 N HCl in a mixed solvent of THF and Et2O to give the title compound (147 mg) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 9.20 (s, 1H), 7.40 (d, 1H), 6.98 (s, 1H), 7.70 (m, 3H), 6.25 (d, 1H), 4.30–4.06 (m, 6H), 3.60–3.30 (m, 4H), 3.15 (m, 4H), 3.00–2.70 (, 4H), 2.00–1.60 (m, 6H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07160888B2 |
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| Source dataset | uspto-grants-2007_01 |
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| ORD ID | ord-304444adade74457a572ba1024204ae5 |
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| Source note | uspto-grants-2007_01 |
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