Triethylamine → [1-(4-Methoxyphenyl)ethyl]-2-methylpteridin-4-yl-amine

HRID 1255884

반응식

HRID 1255884 반응식
Cl[C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH2:9])[C:3]=1[NH2:10].O1CCO[CH:13](O)[CH:12]1O.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([CH:27]([NH2:29])[CH3:28])=[CH:23][CH:22]=1.C(N(CC)CC)C>CCO.CCCCCC.CCOC(C)=O>[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([CH:27]([NH:29][C:2]2[C:3]3[C:4](=[N:9][CH:12]=[CH:13][N:10]=3)[N:5]=[C:6]([CH3:8])[N:7]=2)[CH3:28])=[CH:23][CH:22]=1

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 961701,4-Dioxane-2,3-diolHCID 2381811-(4-Methoxyphenyl)ethanamineHCID 5941456-Chloro-2-methylpyrimidine-4,5-diamine

생성물 1

HCID 58174228[1-(4-Methoxyphenyl)ethyl]-2-methylpteridin-4-yl-amine수율 21.3%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 21226206Ethyl acetate hexane용매

반응 조건

온도
25 °C

실험 절차

A mixture of 6-chloro-4,5-diamino-2-methylpyrimidine (317 mg, 2.0 mmol) and 1,4-dioxane-2,3-diol (240 mg, 2.0 mmol) in EtOH (15 mL) was stirred at 25° C. for 1 h. TLC analysis (1:1 hexane/EtOAc on SiO2) indicated complete consumption of starting material. 1-(4-Methoxyphenyl)-ethylamine (332 mg, 2.2 mmol) and triethylamine (Et3N, 0.3 mL, 2.2 mmol) were added, and the reaction was stirred overnight. The majority of solvent was removed in vacuo and the residue was partitioned between EtOAc and H2O. The organic layer was concentrated in vacuo to leave a brown residue that was purified by column chromatography over SiO2, eluting with 2:1 EtOAc/hexane, then 100% EtOAc to afford [1-(4-methoxyphenyl)ethyl]-2-methylpteridin-4-yl-amine (126 mg) as a brown oil.

후처리

  1. customconsumption of starting material
  2. stirringthe reaction was stirred overnight
  3. customThe majority of solvent was removed in vacuo
  4. customthe residue was partitioned between EtOAc and H2O
  5. concentrationThe organic layer was concentrated in vacuo
  6. customto leave a brown residue that
  7. customwas purified by column chromatography over SiO2
  8. washeluting with 2:1 EtOAc/hexane

출처 및 근거

ORD 기록
ord-2d652c990f454b36b30dbadce40fb6c8
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08461164B2

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