Ethyl oxoacetate → 2,4-Bis[[(2,3-difluorophenyl)methyl]thio]-7(8h)-pteridinone

HRID 1814239ノート

反応式

HRID 1814239 の反応式
[Na].[NH2:2][C:3]1[C:4]([SH:11])=[N:5][C:6]([SH:10])=[N:7][C:8]=1[NH2:9].[F:12][C:13]1[C:20]([F:21])=[CH:19][CH:18]=[CH:17][C:14]=1[CH2:15]Br.C([O:26][CH2:27][CH3:28])(=O)C=O>CO>[F:12][C:13]1[C:20]([F:21])=[CH:19][CH:18]=[CH:17][C:14]=1[CH2:15][S:10][C:6]1[N:5]=[C:4]([S:11][CH2:15][C:14]2[CH:17]=[CH:18][CH:19]=[C:20]([F:21])[C:13]=2[F:12])[C:3]2[N:2]=[CH:28][C:27](=[O:26])[NH:9][C:8]=2[N:7]=1

参加物

6

反応物 4

HCID 70211Ethyl oxoacetateHCID 5179841-(Bromomethyl)-2,3-difluoro-benzeneHCID 5360545Sodium2 回HCID 178509065HCID 178509065、化合物

生成物 1

HCID 225060122,4-Bis[[(2,3-difluorophenyl)methyl]thio]-7(8h)-pteridinone

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Sodium (3.96 g) was dissolved in methanol (150 ml), 5,6-diamino-2,4-pyrimidinedithiol (15 g) was added, then 2,3-difluorobenzylbromide (30.9 g) slowly added and the reaction mixture was stirred at room temperature under nitrogen for 10 min. Ethyl glyoxalate (15 ml) was added followed by more sodium (2.5 g) and the reaction was left for a further 20 min. The reaction was then quenched with acetic acid (10 ml) and poured on to water (600 ml) with stirring. The resulting precipitate was filtered through celite and washed with water. The filtrate was discarded and the solid was washed through the celite using acetone. The solution was then evaporated to dryness and purified by silica gel column chromatography using 10% ethyl acetate in DCM to yield the sub-titled compound as a cream solid (8 g).

後処理

  1. waitthe reaction was left for a further 20 min
  2. customThe reaction was then quenched with acetic acid (10 ml)
  3. additionpoured on to water (600 ml)
  4. stirringwith stirring
  5. filtrationThe resulting precipitate was filtered through celite
  6. washwashed with water
  7. washthe solid was washed through the celite
  8. customThe solution was then evaporated to dryness
  9. custompurified by silica gel column chromatography

出典と根拠

ORDレコード
ord-45486d3bdec14dd39efd99888d4d42a8
出典データセット
uspto-grants-2005_04
特許番号
US06875868B2

反応ノート

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