Potassium Carbonate → 3-(4-methoxybenzyl)-1-benzyl-6-chloro-3,4-dihydroquinazolin-2(1H)-one

HRID 545629ノート

反応式

HRID 545629 の反応式
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7][NH:8][CH2:9][C:10]2[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=2Br)=[CH:5][CH:4]=1.C([O-])([O-])=O.[K+].[K+].[CH2:26]([N:33]=[C:34]=[O:35])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CN(C=O)C>[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7][N:8]2[CH2:9][C:10]3[C:11](=[CH:12][CH:13]=[C:14]([Cl:16])[CH:15]=3)[N:33]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:34]2=[O:35])=[CH:5][CH:4]=1

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 76639Benzyl isocyanateHCID 66158876HCID 66158876、化合物

生成物 1

HCID 671889683-(4-methoxybenzyl)-1-benzyl-6-chloro-3,4-dihydroquinazolin-2(1H)-one

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

To a stirring mixture of N-(4-methoxybenzyl)(2-bromo-5-chlorophenyl)methanamine (0.94 g, 2.77 mmol), Pd(PPh3)4 (0.32 g, 0.277 mmol), and K2CO3 (0.77 g, 5.55 mmol) was added DMF (5.0 mL), followed by slow addition of benzyl isocyanate (0.38 mL, 3.05 mmol) at 0° C. The mixture was heated at 120° C. for 4 hrs. The resulting mixture was concentrated and passed through a short path of silica gel and eluted with DCM until the product eluted. The combined organic layers were concentrated to give the product 3-(4-methoxybenzyl)-1-benzyl-6-chloro-3,4-dihydroquinazolin-2(1H)-one as a pale yellow foam. MS m/e 340 (M+H)+.

後処理

  1. concentrationThe resulting mixture was concentrated
  2. washeluted with DCM until the product
  3. washeluted
  4. concentrationThe combined organic layers were concentrated

出典と根拠

ORDレコード
ord-3745554f7bb44bcd8985aa7ec01b93b3
出典データセット
uspto-grants-2011_05
特許番号
US07935709B2

反応ノート

読み込み中…