Iodoethane → N-ethyl-4-[(2,4-diamino-5-pyrimidinyl)-methyl]-2,6-dimethoxy-carbanilic acid ethyl ester

HRID 462542ノート

反応式

HRID 462542 の反応式
[CH2:1]([O:3][C:4](=[O:25])[NH:5][C:6]1[C:11]([O:12][CH3:13])=[CH:10][C:9]([CH2:14][C:15]2[C:16]([NH2:22])=[N:17][C:18]([NH2:21])=[N:19][CH:20]=2)=[CH:8][C:7]=1[O:23][CH3:24])[CH3:2].[H-].[Na+].[CH2:28](I)[CH3:29]>CN(C)C=O>[CH2:1]([O:3][C:4](=[O:25])[N:5]([CH2:28][CH3:29])[C:6]1[C:11]([O:12][CH3:13])=[CH:10][C:9]([CH2:14][C:15]2[C:16]([NH2:22])=[N:17][C:18]([NH2:21])=[N:19][CH:20]=2)=[CH:8][C:7]=1[O:23][CH3:24])[CH3:2]

参加物

5

反応物 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 540837614-[(2,4-Diamino-5-pyrimidinyl)-methyl]-2,6-dimethoxy-carbanilic acid ethyl ester

生成物 1

HCID 53828440N-ethyl-4-[(2,4-diamino-5-pyrimidinyl)-methyl]-2,6-dimethoxy-carbanilic acid ethyl ester

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 12 g. of 4-[(2,4-diamino-5-pyrimidinyl)-methyl]-2,6-dimethoxycarbanilic acid ethyl ester and 2 g. of sodium hydride (50% dispersion in oil) in 100 ml. of absolute dimethylformamide was stirred at room temperature for 4 hours and then treated with 6.5 g. of ethyl iodide. After stirring at room temperature for 30 minutes, the dimethylformamide was removed at 60° C. under vacuum. The residue was taken up in 250 ml. of water and the precipitated product extracted with two 600 ml. portions of ethyl acetate. The ethyl acetate extract was washed with two 300 ml. portions of water, dried over magnesium sulfate and evaporated under vacuum. The residue was chromatographed on 350 g. of silica gel using ethyl acetate/alcohol (3:1) and there was obtained N-ethyl-4-[(2,4-diamino-5-pyrimidinyl)-methyl]-2,6-dimethoxy-carbanilic acid ethyl ester having a melting point of 165°-167° C. (recrystallization from ethyl acetate).

後処理

  1. additionA mixture of 12 g
  2. additiontreated with 6.5 g
  3. customthe dimethylformamide was removed at 60° C. under vacuum
  4. extractionof water and the precipitated product extracted with two 600 ml
  5. extractionThe ethyl acetate extract
  6. washwas washed with two 300 ml
  7. dry with materialportions of water, dried over magnesium sulfate
  8. customevaporated under vacuum
  9. customThe residue was chromatographed on 350 g

出典と根拠

ORDレコード
ord-9f343d0a650a492ca75b877d8f9bfd69
出典データセット
uspto-grants-1985_05
特許番号
US04515948

反応ノート

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