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

HRID 339795

反応式

HRID 339795 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 21226206Ethyl acetate hexane溶媒

反応条件

温度
25 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f24ae463ec024ff493a47364f93602d2
出典データセット
uspto-grants-2014_11
特許番号
US08895568B2

関連ノート

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