Bromine → HCID 18613734、化合物

HRID 1264910ノート

反応式

HRID 1264910 の反応式
[CH2:1]([C:3]1[N:4]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[C:5](=[O:13])[C:6]2[CH:12]=[CH:11][CH:10]=[N:9][C:7]=2[N:8]=1)[CH3:2].C([O-])(=O)C.[Na+].[Br:26]Br>C(O)(=O)C>[Br:26][CH:1]([C:3]1[N:4]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[C:5](=[O:13])[C:6]2[CH:12]=[CH:11][CH:10]=[N:9][C:7]=2[N:8]=1)[CH3:2]

参加物

5

反応物 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 186137392-Ethyl-3-(4-fluorophenyl)pyrido[2,3-d]pyrimidin-4(3H)-one

生成物 1

HCID 18613734HCID 18613734、化合物収率 85.1%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒2 回

反応条件

温度
40 °C

実験手順

A suspension of the quinazolinone (17) (50.0 g, 0.56 mmol) and anhydrous sodium acetate (56 mg) in glacial acetic acid (1.0 mL) was heated to 40° C. and treated dropwise with a solution of bromine (90 mg, 0.56 mmol) in glacial acetic acid (5 mL). Once the starting material was fully consumed by TLC analysis, the mixture was poured onto water (5 mL), basified with saturated aqueous sodium hydrogen carbonate and extracted with tert-butylmethyl ether. The combined organic phases were dried (MgSO4), filtered, and concentrated to a solid which was purified by silica-gel column chromatography [eluent: Ethyl acetate:Hexane, 50:50, v/v] to give the title bromide (18) (166 mg, 85%) as an off white solid:

後処理

  1. customOnce the starting material was fully consumed by TLC analysis
  2. additionthe mixture was poured onto water (5 mL)
  3. extractionextracted with tert-butylmethyl ether
  4. dry with materialThe combined organic phases were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated to a solid which
  7. customwas purified by silica-gel column chromatography [eluent

出典と根拠

ORDレコード
ord-9c5a14bf72f64e0bb9dc9b9ddf6a0062
出典データセット
uspto-grants-2003_04
特許番号
US06545005B1

反応ノート

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