Diisopropylethylamine → (S)-tert-butyl 3-(2-chloro-5-fluoropyrimidin-4-ylamino)pyrrolidine-1-carboxylate

HRID 74884

반응식

HRID 74884 반응식
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([F:9])=[CH:4][N:3]=1.CCN(C(C)C)C(C)C.[NH2:19][C@H:20]1[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21]1>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([NH:19][C@H:20]2[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21]2)[C:5]([F:9])=[CH:4][N:3]=1

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 2507052,4-Dichloro-5-fluoropyrimidineHCID 854071tert-butyl (3S)-3-aminopyrrolidine-1-carboxylate

생성물 1

HCID 86667413(S)-tert-butyl 3-(2-chloro-5-fluoropyrimidin-4-ylamino)pyrrolidine-1-carboxylate수율 102.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a mixture of 2,4-dichloro-5-fluoro-pyrimidine (1.75 g, 10.48 mmol) and iPr2NEt (3.27 mL, 18.78 mmol) in THF (50 mL) was added tert-butyl (3S)-3-aminopyrrolidine-1-carboxylate (1.83 mL, 10.48 mmol) in THF (2 mL). The resulting solution was allowed to stir at room temperature for 2 hours. The mixture was concentrated to dryness, diluted with dichloromethane and washed with water. The organic layer was dried over Na2SO4 and concentrated in vacuo to afford 3.41 g of 7a, as a white foamy solid.

후처리

  1. concentrationThe mixture was concentrated to dryness
  2. additiondiluted with dichloromethane
  3. washwashed with water
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-e47b03ca24134a80b0e8ae90c3bb248d
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829007B2

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