Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Boron tribromide | HCID 25134 | — |
| Reactant | 2-chloro-N-(4-methoxyphenyl)-N-methylquinazolin-4-amine | HCID 11738112 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 11460340 | HCID 11460340 | 59.7% |
Reaction Steps
To a solution of (2-chloro-quinazolin-4-yl)-(4-methoxy-phenyl)-methyl-amine (100 mg, 0.334 mmol) in 30 ml dichloromethane cooled at −20° C. was added slowly 60 μl of BBr3 (0.668 mmol). The reaction mixture was stirred at −20° C. for 2 h then it was warmed to room temperature. It was stirred another 2 h at this temperature. The reaction mixture was diluted with ethyl acetate (50 ml) and washed with cold 5% sodium bicarbonate. The organic phase was dried and concentrated. The residue was purified by a small silica column using ethyl acetate and hexane (1:3) as eluents to give the product (57 mg, 57%). 1H NMR (CDCl3): 7.65-7.56 (m, 2H), 7.04-6.87 (m, 5H), 3.59 (s, 3H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07618975B2 |
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| Source dataset | uspto-grants-2009_11 |
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| ORD ID | ord-681fe0d2ddd0417bb1591750d807bf5e |
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| Source note | uspto-grants-2009_11 |
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