Sodium Hydroxide → 4-[(4-Pyrazin-2-yl-pyrimidin-2-ylamino)-methyl]-benzoic acid

HRID 416226

反応式

HRID 416226 の反応式
O.O.C[O:4][C:5](=[O:17])[C:6]1[CH:11]=[CH:10][C:9]([CH2:12][NH:13][C:14]([NH2:16])=[NH:15])=[CH:8][CH:7]=1.CN(/[CH:21]=[CH:22]/[C:23]([C:25]1[CH:30]=[N:29][CH:28]=[CH:27][N:26]=1)=O)C.C[O-].[Na+].[OH-].[Na+]>CO.O>[N:26]1[CH:27]=[CH:28][N:29]=[CH:30][C:25]=1[C:23]1[CH:22]=[CH:21][N:16]=[C:14]([NH:13][CH2:12][C:9]2[CH:10]=[CH:11][C:6]([C:5]([OH:4])=[O:17])=[CH:7][CH:8]=2)[N:15]=1

参加物

7

反応物 4

HCID 14798Sodium HydroxideHCID 5825354(E)-3-(Dimethylamino)-1-(pyrazin-2-YL)prop-2-EN-1-oneHCID 10942334Sodium MethoxideHCID 1784979354-Guanidinomethyl-benzoic acid methyl ester dihydrate

生成物 1

HCID 666221674-[(4-Pyrazin-2-yl-pyrimidin-2-ylamino)-methyl]-benzoic acid収率 87.6%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒3 回HCID 962Water溶媒

実験手順

A suspension of 24 (6.2 g, 25.4 mmol) and 23a (3.0 g, 16.9 mmol) in anhydrous methanol (40 mL) was stirred and heated to reflux for 10 min, then a solution of sodium methoxide 95% (3.65 g, 67.6 mmol) in methanol (40 mL) was slowly added. After refluxing for 24 h, 20 mL of 2.5N NaOH in water were added and the refluxing was maintained for additional 24 h. The mixture was allowed to cool to the room temperature methanol was removed under reduced pressure, 100 mL of water were added and the resultant mixture was extracted with AcOEt. The aqueous phase was separated and acidified to pH 5-6 with 2N HCl to form a precipitate which was collected by filtration, rinsed with water and dried to afford the desired carboxylic acid 25a (4.55 g, 14.8 mmol, 87%) as a white solid.

後処理

  1. temperatureheated
  2. temperatureto reflux for 10 min
  3. temperatureAfter refluxing for 24 h
  4. temperaturethe refluxing was maintained for additional 24 h
  5. customwas removed under reduced pressure, 100 mL of water
  6. additionwere added
  7. extractionthe resultant mixture was extracted with AcOEt
  8. customThe aqueous phase was separated
  9. customto form a precipitate which
  10. filtrationwas collected by filtration
  11. washrinsed with water
  12. customdried

出典と根拠

ORDレコード
ord-8255c106f0b44dbfb641b883bd9a1899
出典データセット
uspto-grants-2012_01
特許番号
US08088805B2

関連ノート

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