Sodium Chloride → (2S)-1-(4-(3-iodo-1-isopropyl-1H-pyrazol-4-yl)pyrimidin-2-ylamino)propan-2-ol

HRID 500713노트

반응식

HRID 500713 반응식
[I:1][C:2]1[C:6]([C:7]2[CH:12]=[CH:11][N:10]=[C:9](S(C)(=O)=O)[N:8]=2)=[CH:5][N:4]([CH:17]([CH3:19])[CH3:18])[N:3]=1.[NH2:20][CH2:21][C@@H:22]([OH:24])[CH3:23].CCCCCC.[Na+].[Cl-]>C1COCC1.CCOC(C)=O>[I:1][C:2]1[C:6]([C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH:20][CH2:21][C@@H:22]([OH:24])[CH3:23])[N:8]=2)=[CH:5][N:4]([CH:17]([CH3:19])[CH3:18])[N:3]=1

참가 물질

7

반응물 4

HCID 5234Sodium ChlorideHCID 8058HexaneHCID 7311736(S)-(+)-1-Aminopropan-2-olHCID 578563434-(3-iodo-1-isopropyl-1H-pyrazol-4-yl)-2-(methylsulfonyl)pyrimidine

생성물 1

HCID 57856239(2S)-1-(4-(3-iodo-1-isopropyl-1H-pyrazol-4-yl)pyrimidin-2-ylamino)propan-2-ol수율 96.9%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매2회

실험 절차

A mixture of 4-(3-iodo-1-isopropyl-1H-pyrazol-4-yl)-2-(methylsulfonyl)pyrimidine B-1-2 (16 g, 40 mmol) and (s)-1-amino-propan-2-ol (9 g, 122 mmol) in THF (160 mL) was heated to reflux overnight. TLC (hexane: EtOAc=2:1) showed the reaction was complete, EtOAc (80 mL) and saturated aqueous NaCl (80 mL) were added to the mixture, and the layers were separated. The organic layer was separated, washed with saturated aqueous NaCl (30 mL), dried over Na2SO4 and concentrated to give (2S)-1-(4-(3-iodo-1-isopropyl-1H-pyrazol-4-yl)pyrimidin-2-ylamino)propan-2-ol (B-1-3) (15 g, 96.9%) as a brown oil.

후처리

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. customthe layers were separated
  4. customThe organic layer was separated
  5. washwashed with saturated aqueous NaCl (30 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-1d4dff21e95d43808fb2a1eabfc04537
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07772246B2

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