Tert-Butylamine → 2,4-Dichloro-pyrimidine-5-carboxylic acid-tert-butylamide

HRID 970424

反応式

HRID 970424 の反応式
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([C:9](Cl)=[O:10])=[CH:4][N:3]=1.[C:12]([NH2:16])([CH3:15])([CH3:14])[CH3:13].C(N(CC)CC)C>C1COCC1>[C:12]([NH:16][C:9]([C:5]1[C:6]([Cl:8])=[N:7][C:2]([Cl:1])=[N:3][CH:4]=1)=[O:10])([CH3:15])([CH3:14])[CH3:13]

参加物

5

反応物 3

HCID 6385Tert-ButylamineHCID 8471TriethylamineHCID 137841122,4-Dichloropyrimidine-5-carbonyl chloride

生成物 1

HCID 223267522,4-Dichloro-pyrimidine-5-carboxylic acid-tert-butylamide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-10 °C

実験手順

A solution of 24.85 g (117.5 mmol) of 2,4-dichloro-pyrimidine-5-carbonyl chloride in 125 ml of THF is cooled to −15° C. It is slowly mixed with a solution of 13.2 ml (124.5 mmol) of tert-buylamine and 17.4 ml (125.7 mmol) of triethylamine in 50 ml of THF, so that the temperature of the reaction mixture remains less than −10° C. It is stirred for another 2 hours at −10° C., then the cooling bath is removed, and the reaction mixture is heated to room temperature while being stirred. After 1 hour, the precipitate that is formed is filtered off, and the filtrate is completely concentrated by evaporation. The residue that is obtained is purified by chromatography (hexane/ethyl acetate 4:1). 14.01 g (56.6 mmol, corresponding to 50% of theory) of the product is obtained.

後処理

  1. customremains less than −10° C
  2. customthe cooling bath is removed
  3. temperaturethe reaction mixture is heated to room temperature
  4. stirringwhile being stirred
  5. waitAfter 1 hour
  6. customthe precipitate that is formed
  7. filtrationis filtered off
  8. concentrationthe filtrate is completely concentrated by evaporation
  9. customThe residue that is obtained
  10. customis purified by chromatography (hexane/ethyl acetate 4:1)
  11. custom14.01 g (56.6 mmol, corresponding to 50% of theory) of the product is obtained

出典と根拠

ORDレコード
ord-c9ce549a9b4a400299e4e4993e01a424
出典データセット
uspto-grants-2007_12
特許番号
US07312225B2

関連ノート

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