関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Hexane | HCID 8058 | — |
| 反応物 | Ethyl Acetate | HCID 8857 | — |
| 反応物 | 4-(Dimethylamino)butan-1-ol | HCID 83350 | — |
| 反応物 | N-(3-Bromophenyl)-7-fluoro-6-nitroquinazolin-4-amine | HCID 10761182 | — |
| 溶媒 | Tetrahydrofuran | HCID 8028 | — |
| 溶媒 | Methylenechloride Hexane | HCID 21226440 | — |
| 溶媒 | Ethylacetate methanol | HCID 21584119 | — |
| 生成物 | 6-amino-4-[(3-bromophenyl)amino]-7-[4-(N,N-dimethylamino)butyloxy]quinazoline | HCID 10693912 | 33% |
反応手順
To a suspension of hexane prewashed sodium hydride (11.0 mmol, 440 mg of a 60% dispersion in mineral oil) in THF (20 mL) was cannulated a solution of 4-(N,N-dimethylamino)butan-1-ol (8.80 mmol, 1.03 g) in THF (30 mL). The resulting suspension was stirred at 20° C. under N2 for 2 hours and then cannulated into a solution of 4-[(3-bromophenyl)amino]-7-fluoro-6-nitroquinazoline (J Med Chem, 1996;39:918-928) (0.80 g, 2.20 mmol) in THF (30 mL) under N2. The dark red solution was then heated at reflux overnight. Identical workup as above gave, after chromatography on grade III alumina eluting with EtOAc to MeOH/EtOAc (5:95) to give 6-amino-4-[(3-bromophenyl)amino]-7-[4(N,N-dimethylamino)butyloxy]quinazoline (310 mg, 33%) as a pale brown powder, mp (CH2Cl2/hexane) 155-156° C.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US06344459B1 |
|---|
| 出典データセット | uspto-grants-2002_02 |
|---|
| ORD ID | ord-338a8fee1d5d47ad95776c56a158f484 |
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| 出典メモ | uspto-grants-2002_02 |
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