Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Lithium Hydroxide | HCID 3939 | — |
| Reactant | HCID 67539629 | HCID 67539629 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 67539196 | HCID 67539196 | 63% |
Reaction Steps
To a solution of (7S)-4-[7-Methyl-8-(3,3,3-trifluoro-2-methoxy-2-phenyl-propionyl)-5,6,7,8-tetrahydro-pyrido[2,3-d]pyrimidin-4-yl]-piperazine-1-carboxylic acid tert-butyl ester (84 mg, 0.153 mmol) in MeOH (5 mL) was added LiOH (3M, 4 mL). The mixture was stirred at room temperature for 4 days and then neutralized with 2N HCl. The solvent was removed and the residue was subject to column chromatography, eluted by ethyl acetate—DCM/MeOH (20:1) to afford (7S)-4-(7-Methyl-5,6,7,8-tetrahydro-pyrido[2,3-d]pyrimidin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester (32 mg, 63%). 1H NMR (CDCl3, 400 MHz) δ 8.11 (s, 1H), 5.20 (s, 1H), 3.54 (m, 5H), 3.30 (m, 4H), 2.57 (m, 2H), 1.95 (m, 1H), 1.48 (s, 9H), 1.40 (m, 1H), 1.27 (d, J=6.4 Hz, 3H). MS (APCI+) [M+H]+334.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08680114B2 |
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| Source dataset | uspto-grants-2014_03 |
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| ORD ID | ord-8b3185c3b58a4ee1bb0011512d36fd0d |
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| Source note | uspto-grants-2014_03 |
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