Triethylamine → n-[4'-(2,4-Diamino-pyrimidin-5-ylmethyl)-2',6'-diethoxy-biphenyl-3-yl]-methanesulphonamide

HRID 2416338ノート

反応式

HRID 2416338 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]([O:14][CH2:15][CH3:16])=[CH:12][C:11]([CH2:17][C:18]3[C:19]([NH2:25])=[N:20][C:21]([NH2:24])=[N:22][CH:23]=3)=[CH:10][C:9]=2[O:26][CH2:27][CH3:28])[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[CH3:36][S:37](Cl)(=[O:39])=[O:38]>CN(C)C=O>[NH2:24][C:21]1[N:20]=[C:19]([NH2:25])[C:18]([CH2:17][C:11]2[CH:12]=[C:13]([O:14][CH2:15][CH3:16])[C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([NH:1][S:37]([CH3:36])(=[O:39])=[O:38])[CH:3]=3)=[C:9]([O:26][CH2:27][CH3:28])[CH:10]=2)=[CH:23][N:22]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 98646205-(3'-Amino-2,6-diethoxy-biphenyl-4-ylmethyl)-pyrimidine-2,4-diamine

生成物 1

HCID 22636769n-[4'-(2,4-Diamino-pyrimidin-5-ylmethyl)-2',6'-diethoxy-biphenyl-3-yl]-methanesulphonamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
0 °C

実験手順

5-(3′-Amino-2,6-diethoxy-biphenyl-4-ylmethyl)-pyrimidine-2,4-diamine (228 mg; 0.6 mmol) is dissolved in dimethylformamide (6 ml; dried over a molecular sieve), triethylamine (0.090 ml; 0.66 mmol) is added at room temperature, and the mixture is cooled to 0° C. and a solution of methanesulphonyl chloride (0.051 ml; 0.66 mmol) in dimethylformamide (1.0 ml) is added in the course of 5 minutes. After 1 hour at 0-5° C. the reaction mixture is concentrated and the residue is taken up in water, after which the pH is adjusted to 10 by addition of NH4OH conc. After stirring for 15 minutes the mixture is filtered with suction and the residue is dried under a high vacuum and chromatographed over silica gel (60 g) with methylene chloride/methanol/NH4OH conc. (19/1/0.05).

後処理

  1. additionis added at room temperature
  2. concentrationAfter 1 hour at 0-5° C. the reaction mixture is concentrated
  3. additionafter which the pH is adjusted to 10 by addition of NH4OH conc.
  4. filtrationis filtered with suction
  5. customthe residue is dried under a high vacuum
  6. customchromatographed over silica gel (60 g) with methylene chloride/methanol/NH4OH conc. (19/1/0.05)

出典と根拠

ORDレコード
ord-bc344275c5ad4d4dbb7bd28ba6ee2f3f
出典データセット
uspto-grants-2004_11
特許番号
US06821980B1

反応ノート

読み込み中…