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Sodium Chloride → (2R,3R)-3-(2-Chloro-5-trifluoromethylpyrimidin-4-ylamino)butan-2-ol

HRID 548963
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HRID 548963 반응식
C(N(CC)CC)C.[Cl:8][C:9]1[N:14]=[C:13](Cl)[C:12]([C:16]([F:19])([F:18])[F:17])=[CH:11][N:10]=1.Cl.[NH2:21][C@H:22]([CH3:26])[C@H:23]([OH:25])[CH3:24].[Na+].[Cl-]>C(#N)C>[Cl:8][C:9]1[N:14]=[C:13]([NH:21][C@H:22]([CH3:26])[C@H:23]([OH:25])[CH3:24])[C:12]([C:16]([F:19])([F:18])[F:17])=[CH:11][N:10]=1
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참가 물질

6

반응물 4

HCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 27827742,4-Dichloro-5-(trifluoromethyl)pyrimidineHCID 86618937(2R,3R)-3-aminobutan-2-ol hydrochloride

생성물 1

HCID 59683169(2R,3R)-3-(2-Chloro-5-trifluoromethylpyrimidin-4-ylamino)butan-2-ol수율 31%

시약·촉매·용매 1

HCID 6342
Acetonitrile
용매

실험 절차

4.8 ml (34.8 mmol) of triethylamine are added dropwise to 3.78 g (17.4 mmol) of 2,4-dichloro-5-trifluoromethylpyrimidine and 2.19 g (17.4 mmol) of (2R,3R)-3-amino-butan-2-ol hydrochloride in 70 ml of acetonitrile at 0° C. The mixture is slowly warmed to room temperature and then stirred for 48 hours. The mixture is added to half-concentrated NaCl solution and extracted with ethyl acetate. The combined organic phases are dried (Na2SO4), filtered and concentrated. The resulting residue is purified by HPLC. 1.45 g (5.4 mmol; 31% yield) of the product are obtained.

후처리

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic phases are dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting residue is purified by HPLC
  6. custom1.45 g (5.4 mmol; 31% yield) of the product are obtained

출처 및 근거

ORD 기록
ord-0801027a205b4722b0ab9f70c1929a00
출처 데이터셋
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07943629B2

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