Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Sodium cyanoborohydride | HCID 5003444 | — |
| Reactant | HCID 11471935 | HCID 11471935 | — |
| Reactant | Formaldehyde--water (1/1) | HCID 22136924 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 11529870 | HCID 11529870 | 68.8% |
Reaction Steps
To a mixture of (6-amino-2-methyl-quinazolin-4-yl)-(4-methoxy-phenyl)-methylamine (16 mg, 0.05 mmol), 2 ml of 37% formaldehyde water solution and sodium cyanoborohydride (6.3 mg, 0.1 mmol) was added 2 N HCl (0.05 ml) at 0° C. The reaction mixture was stirred for 1 h at 0° C., then diluted by EtOAc (10 ml), washed with saturated NaHCO3 aq., brine, dried over Na2SO4, filtered and concentrated by vacuum. The crude product was purified by chromatography on silica gel with acetate, hexane (1:3 to 1:1) as eluent, yielding 11 mg of title compound (68.8%) as yellow solids. 1H NMR (CDCl3): 7.63 (d, J=9.0 Hz, 1H), 7.20-7.12 (m, 3H), 6.91-6.88 (m, 2H), 6.23 (d, J=2.7 Hz, 1H), 3.80 (s, 3H), 3.57 (s, 3H), 2.69 (s, 3H), 2.62 (s, 6H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08258145B2 |
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| Source dataset | uspto-grants-2012_09 |
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| ORD ID | ord-27c80419853e4f60959d5ce178929af3 |
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| Source note | uspto-grants-2012_09 |
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