Dichloromethane → 4-[1-(2,2-Difluoroethyl)-3-iodo-1H-pyrazol-4-yl]-2-(methylthio)pyrimidine

HRID 500733

반응식

HRID 500733 반응식
[I:1][C:2]1[NH:6][N:5]=[CH:4][C:3]=1[C:7]1[CH:12]=[CH:11][N:10]=[C:9]([S:13][CH3:14])[N:8]=1.C([O-])([O-])=O.[K+].[K+].[F:21][CH:22]([F:25])[CH2:23]I.C(Cl)Cl>CN(C=O)C.CO>[F:21][CH:22]([F:25])[CH2:23][N:5]1[CH:4]=[C:3]([C:7]2[CH:12]=[CH:11][N:10]=[C:9]([S:13][CH3:14])[N:8]=2)[C:2]([I:1])=[N:6]1

참가 물질

7

반응물 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 38335651,1-Difluoro-2-iodoethaneHCID 468641604-(5-Iodo-1H-pyrazol-4-yl)-2-(methylsulfanyl)pyrimidine

생성물 1

HCID 578563034-[1-(2,2-Difluoroethyl)-3-iodo-1H-pyrazol-4-yl]-2-(methylthio)pyrimidine

시약·촉매·용매 2

HCID 887Methanol용매HCID 6228Dimethylformamide용매

실험 절차

To a solution of Intermediate A (83 g, 0.26 mol) in DMF (600 mL) were K2CO3 (58 g, 0.417 mol) and 1,1-difluoro-2-iodo-ethane (60 g, 0.313 mol). Then the mixture was stirred at room temperature overnight. TLC (CH2Cl2: MeOH=20:1) showed the reaction was complete. The mixture was concentrated and the solid was diluted with CH2Cl2 (500 mL). The slurry was filtered and the filtrate was concentrated to give crude product, which was purified via prep. SFC to give compound B-33-1 (41.1 g, 41.3%) as a white solid.

후처리

  1. concentrationThe mixture was concentrated
  2. additionthe solid was diluted with CH2Cl2 (500 mL)
  3. filtrationThe slurry was filtered
  4. concentrationthe filtrate was concentrated
  5. customto give crude product, which
  6. customwas purified via prep
  7. customSFC to give compound B-33-1 (41.1 g, 41.3%) as a white solid

출처 및 근거

ORD 기록
ord-9295e04992444ecf89f3017e5d1f211e
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07772246B2

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