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

HRID 1579316
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HRID 1579316 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 5359268Aluminum2회HCID 232770301-[4-[(2,4-Diaminopyrimidin-5-yl)methyl]-2,6-diethoxyphenyl]-2-methylsulfonylethanone

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-732863ce30e940678da669ce641395cf
출처 데이터셋
uspto-grants-1976_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US03931181

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