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

HRID 970424

반응식

HRID 970424 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-10 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c9ce549a9b4a400299e4e4993e01a424
출처 데이터셋
uspto-grants-2007_12
특허 번호
US07312225B2

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