Dimethylformamide → HCID 86703935、化合物

HRID 1049938ノート

反応式

HRID 1049938 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10](I)[CH:11]=1)[N:8]=[CH:7][N:6]=[C:5]2[NH2:13].[CH3:14][N:15](C)C=O>ClCCl.O.[C-]#N.[Zn+2].[C-]#N.[Pd]>[NH2:13][C:5]1[C:4]2[C:9](=[C:10]([C:14]#[N:15])[CH:11]=[C:2]([Cl:1])[CH:3]=2)[N:8]=[CH:7][N:6]=1

参加物

7

反応物 2

HCID 6228DimethylformamideHCID 86703934HCID 86703934、化合物

生成物 1

HCID 86703935HCID 86703935、化合物

試薬・触媒・溶媒 4

HCID 11186Zinc cyanide (Zn(CN)2)触媒HCID 23938Palladium触媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
110 °C

実験手順

To an 8 mL screw-cap vial was added 6-chloro-8-iodo-quinazolin-4-amine (450 mg, 1.47 mmol), dimethylformamide (2 mL), zinc cyanide (0.65 equiv., 1.0 mmol, 115 mg), and palladium tetra is(triphenylphosphine), (0.1 equiv., 0.15 mmol), 179 mg). The reaction was capped and shaken at 110° C. overnight. The reaction was cooled to room temperature, diluted with 3 mL of dichloromethane, and 2 mL of water was added. The precipitate that followed was collected by filtration, and washed with water, then dichloromethane yielding 240 mg of 4-amino-6-chloro-quinazoline-8-carbonitrile as a light yellow solid. 1H NMR (400 MHz, DMSO) δ 8.72-8.67 (d, J=2.2 Hz, 1H), 8.54-8.50 (s, 1H), 8.50-8.46 (d, J=2.1 Hz, 1H), 8.29-8.22 (bs, 2H). LCMS M/Z (M+H)=205.

後処理

  1. customTo an 8 mL screw-cap vial
  2. customThe reaction was capped
  3. temperatureThe reaction was cooled to room temperature
  4. additionwas added
  5. filtrationThe precipitate that followed was collected by filtration
  6. washwashed with water

出典と根拠

ORDレコード
ord-c5f17549b3104f8b99210cd392333558
出典データセット
uspto-grants-2016_07
特許番号
US09382241B2

反応ノート

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