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Hydrochloric Acid → 4'-[(2,4-Diamino-5-pyrimidinyl)-methyl]-2',6'-diethoxy-acetophenone

HRID 1579316
ノート
印刷プレビュー

反応式

HRID 1579316 の反応式
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH2:9][C:10]2[CH:15]=[C:14]([O:16][CH2:17][CH3:18])[C:13]([C:19](=[O:25])[CH2:20]S(C)(=O)=O)=[C:12]([O:26][CH2:27][CH3:28])[CH:11]=2)=[CH:4][N:3]=1.[Al].Cl>O1CCCC1>[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH2:9][C:10]2[CH:11]=[C:12]([O:26][CH2:27][CH3:28])[C:13]([C:19](=[O:25])[CH3:20])=[C:14]([O:16][CH2:17][CH3:18])[CH:15]=2)=[CH:4][N:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 5359268Aluminum2 回HCID 232770301-[4-[(2,4-Diaminopyrimidin-5-yl)methyl]-2,6-diethoxyphenyl]-2-methylsulfonylethanone

生成物 1

HCID 232763584'-[(2,4-Diamino-5-pyrimidinyl)-methyl]-2',6'-diethoxy-acetophenone

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A suspension of 5.8 g. of 4'-[(2,4-diamino-5-pyrimidinyl)-methyl] -2',6'-diethoxy-2-(methylsulfonyl)acetophenone in 50 ml. of 20% aqueous tetrahydrofuran is reduced with 1 g. of amalgamated aluminum at 65° over a period of 4 hours. (The aluminum chips are immersed in a 2% hydrochloric acid solution for 2 minutes, rinsed with methanol, and thereafter used in the reduction.) The reaction mixture is filtered warm, the filtrate is concentrated and adjusted to a pH of 9 with 5% sodium hydroxide. The resulting solution is then shaken with five 50 ml. portions of ethyl acetate. The resulting crude product after column chromatography (200 g. of silica gel, elution solvent comprising chloroform/N-propanol/concentrated ammonium hydroxide, 80:20:1) yields 4'-[(2,4-diamino-5-pyrimidinyl)-methyl]-2',6'-diethoxy-acetophenone, having a m.p. of 229°-231° recrystallized from methanol.

後処理

  1. additionA suspension of 5.8 g
  2. washrinsed with methanol
  3. filtration) The reaction mixture is filtered
  4. temperaturewarm
  5. concentrationthe filtrate is concentrated
  6. washThe resulting crude product after column chromatography (200 g. of silica gel, elution solvent comprising chloroform/N-propanol/concentrated ammonium hydroxide, 80:20:1)

出典と根拠

ORDレコード
ord-732863ce30e940678da669ce641395cf
出典データセット
uspto-grants-1976_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US03931181

反応ノート

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