Phosphorus oxychloride → 4-Chloro-6-ethyl-5-fluoropyrimidine

HRID 459414노트

반응식

HRID 459414 반응식
[CH2:1]([C:3]1[N:8]=[CH:7][N:6]=[C:5](O)[C:4]=1[F:10])[CH3:2].P(Cl)(Cl)([Cl:13])=O>C(N(CC)CC)C.ClCCl>[Cl:13][C:5]1[C:4]([F:10])=[C:3]([CH2:1][CH3:2])[N:8]=[CH:7][N:6]=1

참가 물질

5

반응물 2

HCID 24813Phosphorus oxychlorideHCID 178437743HCID 178437743, 화합물

생성물 1

HCID 167434454-Chloro-6-ethyl-5-fluoropyrimidine수율 90%

시약·촉매·용매 2

HCID 8471Triethylamine촉매HCID 6344Dichloromethane용매

반응 조건

온도
25 °C

실험 절차

To a mixture of the compound of part (iv) (40 kg), dichloromethane (120 L) and triethylamine (28.4 g) was slowly added phosphorus oxychloride (47.2 kg) over 3 hours maintaining the reaction temperature below 40° C. during the addition. The mixture was heated under reflux for 5 hours, cooled to 25° C. and cautiously quenched into 3N aqueous hydrochloric acid solution (176 L), maintaining the temperature below 20° C. during this operation. The layers were separated, the aqueous phase extracted with dichloromethane (50 L) and the combined organic layers washed with water (50 L). The organic layer was concentrated under reduced pressure to provide the product as an oil (40.69 kg).

후처리

  1. customover 3 hours
  2. temperaturemaintaining the reaction temperature below 40° C.
  3. additionduring the addition
  4. temperatureThe mixture was heated
  5. temperatureunder reflux for 5 hours
  6. customcautiously quenched into 3N aqueous hydrochloric acid solution (176 L)
  7. temperaturemaintaining the temperature below 20° C. during this operation
  8. customThe layers were separated
  9. extractionthe aqueous phase extracted with dichloromethane (50 L)
  10. washthe combined organic layers washed with water (50 L)
  11. concentrationThe organic layer was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-6040693850fa4c84a8190f7c55df5c5e
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07193083B2

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