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

HRID 548963Notes

Reaction equation

HRID 548963 reaction equation
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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-0801027a205b4722b0ab9f70c1929a00
Source dataset
uspto-grants-2011_05
Patent number
US07943629B2

Reaction notes

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