Sodium hydride → (trans)-2-(6-Chloro-2-[(2,3-difluorobenzyl)thio]pyrimidin-4-yl)cyclopentanol

HRID 1025039

反応式

HRID 1025039 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.[C@@H:19]1(O)[CH2:23][CH2:22][CH2:21][C@H:20]1[OH:24].[H-].[Na+]>C1COCC1>[Cl:8][C:6]1[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]=[C:2]([C@@H:19]2[CH2:23][CH2:22][CH2:21][C@H:20]2[OH:24])[CH:7]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 225711trans-1,2-CyclopentanediolHCID 859280374,6-Dichloro-2-((2,3-difluorobenzyl)thio)pyrimidine

生成物 1

HCID 86619895(trans)-2-(6-Chloro-2-[(2,3-difluorobenzyl)thio]pyrimidin-4-yl)cyclopentanol

試薬・触媒・溶媒 1

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 ii), 2.3 g) and (trans)-cyclopentane-1,2-diol (1 g) in THF (50 ml) was added NaH (0.30 g) slowly and the reaction was then allowed to stir for 18 h at RT. The reaction mixture was then partitioned between DCM (150 ml) and H2O (100 ml). The organics were separated and the aqueous layer was re-extracted with DCM (2×150 ml). Organics were combined, dried (MgSO4) and reduced in vacuo and the resulting clear oil was purified by column chromatography on silica gel EtOAc/iso-Hexane (2:8) to give the subtitle compound as a clear colourless oil. Yield 0.94 g

後処理

  1. customThe reaction mixture was then partitioned between DCM (150 ml) and H2O (100 ml)
  2. customThe organics were separated
  3. extractionthe aqueous layer was re-extracted with DCM (2×150 ml)
  4. dry with materialdried (MgSO4)
  5. customthe resulting clear oil was purified by column chromatography on silica gel EtOAc/iso-Hexane (2:8)

出典と根拠

ORDレコード
ord-45e40438d5d249f2b553122fde707295
出典データセット
uspto-grants-2014_05
特許番号
US08722883B2

関連ノート

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