Acetone, oxime → 3-(2,4-Diaminopteridin-6-yl)phenol

HRID 639169ノート

反応式

HRID 639169 の反応式
[OH:1][C:2]1[CH:3]=[C:4]([C:8]([CH:10]=O)=O)[CH:5]=[CH:6][CH:7]=1.CC(=NO)C.S(O)(O)(=O)=O.[NH2:22][C:23]1[N:28]=[C:27]([NH2:29])[C:26]([NH2:30])=[C:25]([NH2:31])[N:24]=1.C(=O)(O)[O-].[Na+]>O.Cl>[NH2:22][C:23]1[N:28]=[C:27]([NH2:29])[C:26]2[C:25](=[N:31][CH:10]=[C:8]([C:4]3[CH:3]=[C:2]([OH:1])[CH:7]=[CH:6][CH:5]=3)[N:30]=2)[N:24]=1

参加物

7

反応物 4

HCID 67180Acetone, oximeHCID 79358Tetraaminopyrimidine sulfateHCID 516892Sodium BicarbonateHCID 129108752-(3-Hydroxyphenyl)-2-oxoacetaldehyde

生成物 1

HCID 177510633-(2,4-Diaminopteridin-6-yl)phenol収率 96.6%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid触媒HCID 962Water溶媒

反応条件

温度
50 °C

実験手順

3-Hydroxyphenylglyoxal (2.10 g, 12.5 mmol) was dissolved in 100 mL of DI water. Acetone oxime (0.912 g, 12.5 mmol) was added, followed by 3 drops of 1N aqueous hydrochloric acid to bring the pH to ca. 2-3. This solution was stirred at 50° C. for one hour, then 2,4,5,6-tetraminopyrimidine sulfate (2.67 g, 11.2 mmol) was added and the reaction mixture was stirred at ambient temperature for 3 hours, then brought to reflux and refluxed for 6 hours. At this point it formed a thick yellow suspension. The reaction was allowed to cool down to ambient temperature. Saturated aqueous sodium bicarbonate was added dropwise to bring the pH to ca. 6-7. The precipitate was collected, washed extensively with water, then with 60 mL of methanol and repeatedly with diethyl ether and dried in vacuo to give 2.75 g of the title compound (96.5% yield) as a light-yellow solid.

後処理

  1. stirringthe reaction mixture was stirred at ambient temperature for 3 hours
  2. temperatureto reflux
  3. temperaturerefluxed for 6 hours
  4. customAt this point it formed a thick yellow suspension
  5. temperatureto cool down to ambient temperature
  6. customThe precipitate was collected
  7. washwashed extensively with water
  8. dry with materialwith 60 mL of methanol and repeatedly with diethyl ether and dried in vacuo

出典と根拠

ORDレコード
ord-443b107d6b7545b496d6540ff8753026
出典データセット
uspto-grants-2010_04
特許番号
US07691858B2

反応ノート

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