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N-[2-[[(2,3-difluorophenyl)methyl]thio]-6-[2-hydroxy-1-(hydroxymethyl)ethoxy]-4-pyrimidinyl]-1-azetidinesulfonamide → 4-Chloro-2-[[(2,3-difluorophenyl)methyl]thio]-6-(1,1-dimethylethoxy)-pyrimidine

HRID 1958918
ノート
印刷プレビュー

反応式

HRID 1958918 の反応式
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([S:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:12]=2[F:18])[N:3]=1.FC1C(F)=CC=CC=1CSC1N=C(NS(N2CCC2)(=O)=O)C=C(OC(CO)CO)N=1.[CH3:49][C:50]([CH3:53])([O-:52])[CH3:51].[K+]>C1COCC1.O>[Cl:8][C:6]1[CH:7]=[C:2]([O:52][C:50]([CH3:53])([CH3:51])[CH3:49])[N:3]=[C:4]([S:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:12]=2[F:18])[N:5]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 11698344N-[2-[[(2,3-difluorophenyl)methyl]thio]-6-[2-hydroxy-1-(hydroxymethyl)ethoxy]-4-pyrimidinyl]-1-azetidinesulfonamideHCID 23665647Potassium tert-butoxide2 回HCID 859280374,6-Dichloro-2-((2,3-difluorobenzyl)thio)pyrimidine

生成物 1

HCID 866198744-Chloro-2-[[(2,3-difluorophenyl)methyl]thio]-6-(1,1-dimethylethoxy)-pyrimidine

試薬・触媒・溶媒 2

HCID 962
Water
溶媒
HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 4,6-Dichloro-2-[(2,3-difluorobenzyl)thio]pyrimidine (the product of example 1 step (2 g) in THF (20 mL) was added potassium tert-butoxide (0.8 g) and the reaction mixture was stirred at ambient temperature for 20 h. Further potassium tert-butoxide (0.8 g) was added and the reaction mixture was stirred at ambient temperature for 411. The mixture was diluted with H2O and extracted with EtOAc (×3). The combined organic layers were washed with H2O and dried (MgSO4), filtered and evaporated. The resulting oil was purified by column chromatography on silica gel using MeOH/DCM (99:1 to 98:2 gradient) as eluent to give the subtitle compound as a clear, colourless oil. Yield: 0.68 g

後処理

  1. stirringthe reaction mixture was stirred at ambient temperature for 411
  2. extractionextracted with EtOAc (×3)
  3. washThe combined organic layers were washed with H2O
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe resulting oil was purified by column chromatography on silica gel

出典と根拠

ORDレコード
ord-8ecea5b4ba3b497fa288faf9a37682cf
出典データセット
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08410123B2

反応ノート

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このページの内容参加物実験手順後処理出典と根拠反応ノート