Water → HCID 57918580, compound

HRID 1908228Notes

Reaction equation

HRID 1908228 reaction equation
Cl.[NH2:2][CH2:3][C@@H:4]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)[OH:5].[Cl:13][C:14]1[CH:19]=[C:18](Cl)[N:17]=[CH:16][N:15]=1.C([O-])(O)=O.[Na+].O>O1CCOCC1>[Cl:13][C:14]1[N:15]=[CH:16][N:17]=[C:18]([NH:2][CH2:3][C@@H:4]([C:6]2[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=2)[OH:5])[CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 709434,6-DichloropyrimidineHCID 516892Sodium BicarbonateHCID 686294101185198-25-7

Product 1

HCID 57918580HCID 57918580, compoundYield 65.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of (R)-2-amino-1-(4-fluoro-phenyl)-ethanol hydrochloride (500 mg, 2.61 mmol), 4,6-dichloropyrimidine (353 mg, 2.37 mmol), and NaHCO3 (1.39 g, 16.6 mmol) in dioxane (10 mL) was heated in a 100° C. bath for 19 h and cooled to rt. Water (10 mL) was added, and the mixture, containing solid, was extracted with CH2Cl2 (3×10 mL). The combined organic extracts were dried (MgSO4) and concentrated. The residue was purified (FCC) to give the title compound as a white solid (415 mg, 59%) in 90% enantiomeric excess (Chiralcel AD-H column, supercritical CO2).

Workup

  1. temperaturecooled to rt
  2. additionthe mixture, containing solid
  3. extractionwas extracted with CH2Cl2 (3×10 mL)
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was purified (FCC)

Sources & evidence

ORD record
ord-7f37cae9da4f4e8db1f992781babd426
Source dataset
uspto-grants-2013_12
Patent number
US08598202B2

Reaction notes

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