Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | Aluminium lithium hydride | HCID 21226445 | — |
| Reactant | HCID 178484582 | HCID 178484582 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 178483682 | HCID 178483682 | — |
Reaction Steps
A solution of 42 mg (0.095 mmol) of cis-3-[4-amino-5-(3-benzyloxy-phenyl)pyrrolo[2,3-d]pyrimidin-7-yl]-cyclobutanecarboxylic acid dimethylamide in 2 ml of anhydrous THF is added dropwise at 0° C. to a 10 mg of lithium aluminium hydride suspended in 2 ml of anhydrous THF. The reaction mixture is slowly warmed to RT overnight. For working-up, the reaction mixture is cooled to 0° C. and then water and a 15% NaOH solution are added in succession thereto. The solution is partitioned between water and ethyl acetate. Drying the organic layer over magnesium sulfate, concentrating in vacuo and purifying by medium-pressure liquid chromatography yield cis-5-(3-benzyloxy-phenyl)-7-(3-dimethylaminomethyl-cyclobutyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine. Analytical HPLC: tR=5.98 min (Grad 2); ES-MS: m/eo=428.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07326699B2 |
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| Source dataset | uspto-grants-2008_02 |
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| ORD ID | ord-ac5531d2b6d74b2495e67d393f6aa1e4 |
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| Source note | uspto-grants-2008_02 |
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