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Sodium Chloride → 4-[(1R,2R)-2-benzyloxy-1-methyl-propoxy]-2-chloro-5-(trifluoromethyl)pyrimidine

HRID 2403561
ノート
印刷プレビュー

反応式

HRID 2403561 の反応式
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=1.[CH2:13]([O:20][C@H:21]([CH3:25])[C@H:22]([OH:24])[CH3:23])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[H-].[Na+].[Cl-].[Na+]>C(OCC)C.C(#N)C>[CH2:13]([O:20][C@H:21]([CH3:25])[C@@H:22]([CH3:23])[O:24][C:6]1[C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 27827742,4-Dichloro-5-(trifluoromethyl)pyrimidineHCID 12695195(2R,3R)-3-(Benzyloxy)butan-2-OL

生成物 1

HCID 468994684-[(1R,2R)-2-benzyloxy-1-methyl-propoxy]-2-chloro-5-(trifluoromethyl)pyrimidine

試薬・触媒・溶媒 2

HCID 3283
Diethyl Ether
溶媒
HCID 6342Acetonitrile溶媒

反応条件

温度
15 °C

実験手順

A solution of 5.00 g (23.0 mmol) of 2,4-dichloro-5-trifluoromethylpyrimidine and 5.40 g (30.0 mmol) of (2R,3R)-3-benzyloxybutan-2-ol in 60 ml of diethyl ether and 65 ml of acetonitrile were admixed at 0° C. with 1.21 g (27.7 mmol) of sodium hydride (55% strength), divided into 3 portions, and then stirred for 90 minutes at 15° C. The mixture was admixed with dilute sodium chloride solution and extracted (3×) with ethyl acetate. The combined organic phases were dried (Na2SO4), filtered and concentrated by evaporation. The resulting residue was purified chromatographically (hexane/ethyl acetate 95:5). This gave 1.60 g (4.4 mmol; yield: 19%) of the product.

後処理

  1. extractionextracted (3×) with ethyl acetate
  2. dry with materialThe combined organic phases were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated by evaporation
  5. customThe resulting residue was purified chromatographically (hexane/ethyl acetate 95:5)

出典と根拠

ORDレコード
ord-e462f77f28b74b0c8056b139958fa0ba
出典データセット
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08802686B2

反応ノート

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