Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Pyrrolidine | HCID 31268 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | 2-[2-Amino-4-(1,3-dihydroisoindole-2-carbonyl)quinazolin-6-yl]benzaldehyde | HCID 59483516 | — |
| Solvent | 1,2-Dichloroethane | HCID 11 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 56943575 | HCID 56943575 | — |
Reaction Steps
100 mg of 2-[2-amino-4-(1,3-dihydroisoindole-2-carbonyl)quinazolin-6-yl]benzaldehyde are dissolved in 2 ml of 1,2-dichloroethane and 2 ml of tetrahydrofuran. 36 μl of pyrrolidine and 15 μl of glacial acetic acid are added, and the mixture is stirred at 60° C. for 6 h. After cooling to 25° C., 170 mg of sodium triacetoxyborohydride are added and stirred at 25° C. for a further 12 h. The mixture is poured into water, extracted three times with dichloromethane, and the combined organic phases are dried over sodium sulfate. After filtration, the filtrate is evaporated to dryness and purified by chromatography (reversed phase HPLC). Yield: 30 mg (26%) of [2-amino-6-(2-pyrrolidin-1-ylmethylphenyl)quinazolin-4-yl]-(1,3-dihydroisoindol-2-yl)methanone; LC-MS retention time: 1.45 min;
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08791129B2 |
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| Source dataset | uspto-grants-2014_07 |
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| ORD ID | ord-7901473be44347fea2765c4e16ffe1e3 |
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| Source note | uspto-grants-2014_07 |
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