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

HRID 500733ノート

反応式

HRID 500733 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9295e04992444ecf89f3017e5d1f211e
出典データセット
uspto-grants-2010_08
特許番号
US07772246B2

反応ノート

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