Methanol → Methyl 5-(2-chloro-4-morpholino-quinazolin-7-yl)furan-2-carboxylate

HRID 517467

反応式

HRID 517467 の反応式
[Cl:1][C:2]1[N:11]=[C:10]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:9]2[C:4](=[CH:5][C:6]([C:18]3[O:22][C:21]([CH:23]=[O:24])=[CH:20][CH:19]=3)=[CH:7][CH:8]=2)[N:3]=1.[C-]#N.[Na+].[CH3:28][OH:29]>C(Cl)(Cl)Cl.[O-2].[Mn+4].[O-2]>[Cl:1][C:2]1[N:11]=[C:10]([N:12]2[CH2:13][CH2:14][O:15][CH2:16][CH2:17]2)[C:9]2[C:4](=[CH:5][C:6]([C:18]3[O:22][C:21]([C:23]([O:29][CH3:28])=[O:24])=[CH:20][CH:19]=3)=[CH:7][CH:8]=2)[N:3]=1

参加物

6

反応物 3

HCID 887MethanolHCID 8929Sodium CyanideHCID 866657705-(2-Chloro-4-morpholino-quinazolin-7-yl)furan-2-carbaldehyde

生成物 1

HCID 86665771Methyl 5-(2-chloro-4-morpholino-quinazolin-7-yl)furan-2-carboxylate収率 79%

試薬・触媒・溶媒 2

HCID 178418406HCID 178418406、化合物触媒HCID 6212Chloroform溶媒

反応条件

温度
0 °C

実験手順

To a 100 mL flask, 5-(2-chloro-4-morpholino-quinazolin-7-yl)furan-2-carbaldehyde (0.6 g, 0.0017 mol) in MeOH (60 mL) was added and cooled to 0° C. To the reaction flask, manganese (IV) oxide (0.74 g, 0.0085 mol) and sodium cyanide (0.429 g, 0.0085 mol) were added at 0° C. The reaction mixture was stirred at 25° C. for 3 h. The reaction mixture was diluted with chloroform and filtered through a pad of Celite® reagent. The filtrate was washed with water, brine, dried over anhydrous sodium sulfate and evaporated under reduced pressure to get the title compound as a solid [0.52 g, 79%]. 1H NMR (300 MHz, CDCl3): δ 8.18 (s, 1H), 7.87-7.86 (m, 2H), 7.29 (d, J=3.6 Hz, 1H), 6.95 (d, J=3.6 Hz, 1H), 3.93 (s, 3H), 3.89 (s, 8H). LC-MS (ESI): Calculated mass: 373.1; Observed mass: 374.1 (RT: 1.57 min).

後処理

  1. filtrationfiltered through a pad of Celite® reagent
  2. washThe filtrate was washed with water, brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-8aa5d8450bd049a088074213efef9ce3
出典データセット
uspto-grants-2015_08
特許番号
US09115092B2

関連ノート

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