Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | HCID 86699682 | HCID 86699682 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 86699683 | HCID 86699683 | 62.5% |
Reaction Steps
To a solution of 2′,4′-dichloro-7′-(4-methoxybenzyl)spiro[cyclopropane-1,5′-pyrrolo[2,3-d]pyrimidin]-6′(7′H)-one (14.0 g, 40.0 mmol) in tetrahydrofuran (200 mL) was added 94% Borane-methyl sulfide complex (8.2 mL, 80.0 mmol) dropwise under nitrogen atmosphere. After the addition was over, the reaction mixture was heated to 60° C. overnight. When the reaction was completed, methanol was added to the reaction solution at 0° C., concentrated in vacuum and the residue was purified by silica gel chromatography to afford the product as a white solid (8.4 g, yield 62.4%). 1H NMR (400 MHz, CDCl3) δ ppm 7.20 (d, J=8.6 Hz, 2H), 6.91-6.86 (m, 2H), 4.59 (s, 2H), 3.81 (s, 3H), 3.48 (s, 2H), 1.71 (q, J=4.9 Hz, 2H), 0.82 (q, J=4.9 Hz, 2H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09428508B2 |
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| Source dataset | uspto-grants-2016_08 |
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| ORD ID | ord-482622e5902d4bbb92c82cf76360732a |
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| Source note | uspto-grants-2016_08 |
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