2-Amino-4,6-dimethyl pyrimidine → Methyl 3-[[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-1-methyl-1H-indole-2-carboxylate

HRID 34993

反応式

HRID 34993 の反応式
[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[N:3]=1.Cl[S:11]([N:14]=[C:15]=[O:16])(=[O:13])=[O:12].[CH3:17][N:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[C:19]1[C:27]([O:29][CH3:30])=[O:28].[Cl-].[Al+3].[Cl-].[Cl-]>[N+](C)([O-])=O.C(Cl)Cl.O>[CH3:9][C:4]1[CH:5]=[C:6]([CH3:8])[N:7]=[C:2]([NH:1][C:15]([NH:14][S:11]([C:20]2[C:21]3[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:18]([CH3:17])[C:19]=2[C:27]([O:29][CH3:30])=[O:28])(=[O:13])=[O:12])=[O:16])[N:3]=1

参加物

8

反応物 4

HCID 130212-Amino-4,6-dimethyl pyrimidineHCID 70918Chlorosulfonyl isocyanateHCID 258548methyl 1-methyl-1H-indole-2-carboxylateHCID 6451240Aluminum(III) Chloride

生成物 1

HCID 14256291Methyl 3-[[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-1-methyl-1H-indole-2-carboxylate収率 23%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 6375Nitromethane溶媒2 回

実験手順

To a stirred suspension of 2.59 g (0.021 mole) of 2-amino-4,6-dimethylpyrimidine in 75 ml dry nitromethane at -10° was added dropwise under nitrogen via syringe 2.0 ml (0.023 mole) of chlorosulfonyl isocyanate at such a rate as to maintain the temperature below 0°. The resulting clear solution was stirred for 0.5 hour at -5° to -10° and then contacted dropwise with a solution of 3.97 g (0.021 mole) of methyl 1-methyl-1H-indole-2-carboxylate dissolved in 40 ml of dry nitromethane. Upon completion of the addition, 2.95 g (0.022 mole) of aluminum (III) chloride was added in one portion. The reaction mixture was stirred at reflux for 3 hours, then cooled to room temperature and poured into 300 ml H2O. Methylene chloride was added and the layers separated. The aqueous solution was extracted with two additional portions of CH2Cl2 and the combined organic solutions were washed with H2O, dried over MgSO4 and evaporated in vacuo. Trituration of the residue with minimal CH2Cl2 afforded 2.02 g of the desired product as a white solid, m.p. 212°-215° (d). The infrared spectrum of the product included absorptions at 3215 and 3150 (NH), 1730 (C=O), 1710 (C=O), 1345 and 1150 (SO2) cm-1. 'H NMR (CDCl3 /DMSO-d6) δ2.43 (s, 6H, pyrimidine CH3), 3.88 (s, 6H, ester CH3 and N--CH3), 6.90 (s, 1H, pyrimidine CH), 7.23-7.75 (m, 3H, indole CH), 8.16-8.47 (m, 1H, indole CH), 10.30 (s, 1H, NH), 13.26 (br s, 1H, NH). Mass spectral analysis showed m/e 123, ##STR30##

後処理

  1. temperatureto maintain the temperature below 0°
  2. additionwas added in one portion
  3. stirringThe reaction mixture was stirred
  4. temperatureat reflux for 3 hours
  5. customthe layers separated
  6. extractionThe aqueous solution was extracted with two additional portions of CH2Cl2
  7. washthe combined organic solutions were washed with H2O
  8. dry with materialdried over MgSO4
  9. customevaporated in vacuo

出典と根拠

ORDレコード
ord-21e2b7a399784639a2152d8427ae5716
出典データセット
uspto-grants-1988_08
特許番号
US04764610

関連ノート

読み込み中…