Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Cyanide | HCID 8929 | — |
| Reactant | (2-Chloromethyl-quinazolin-4-yl)-(4-methoxy-phenyl)-methyl-amine | HCID 11358914 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | HCID 59242022 | HCID 59242022 | — |
Reaction Steps
A mixture of (2-chloromethyl-quinazolin-4-yl)-(4-methoxy-phenyl)-methyl-amine (50 mg, 0.14 mmol) and NaCN (21 mg, 0.43 mmol) in DMSO was heated by microwave for 10 min at 120° C. The reaction was quenched with H2O, diluted with EtOAc and the layers separated. The aqueous phase was extracted with EtOAc (2×5 mL), washed with brine, filtered over Na2SO4 and concentrated. Purification by gradient MPLC (SiO2, EtOAc/hexanes, 0-50%) gave the desired compound. 1H NMR (CDCl3) δ 7.74 (d, 1H), 7.56 (m, 1H), 7.13 (d, 2H), 7.02 (m, 1H), 6.94 (m, 3H), 4.04 (s, 2H), 3.85 (s, 3H), 3.62 (s, 3H); LC-MS (ESI+; 305 ([M+H]+)) and (ESI−; 303 ([M−H]−)).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08309562B2 |
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| Source dataset | uspto-grants-2012_11 |
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| ORD ID | ord-f0e3c5924e0745dcbfb4deabae59a202 |
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| Source note | uspto-grants-2012_11 |
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