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

HRID 500713ノート

反応式

HRID 500713 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1d4dff21e95d43808fb2a1eabfc04537
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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