Hydrochloric Acid → HCID 57888817, compound

HRID 1820268Notes

Reaction equation

HRID 1820268 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[N:6][CH:7]=1.[NH2:8][C@@H:9]([C:13]([OH:15])=[O:14])[CH:10]([CH3:12])[CH3:11].CN(CCO)C.[O-]P([O-])([O-])=O.[K+].[K+].[K+].Cl.C(O)(C(F)(F)F)=O>[Cu]I.O>[CH3:11][CH:10]([CH3:12])[C@@H:9]([NH:8][C:2]1[CH:3]=[N:4][CH:5]=[N:6][CH:7]=1)[C:13]([OH:15])=[O:14]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 79022-(Dimethylamino)ethanolHCID 62657Potassium Phosphate, TribasicHCID 71563D-ValineHCID 783445-Bromopyrimidine

Product 1

HCID 57888817HCID 57888817, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolvent

Procedure

5-Bromopyrimidine (407 mg, 2.56 mmol), D-valine (250 mg, 2.13 mmol), copper(I) iodide (40.6 mg, 0.213 mmol), dimethylaminoethanol (400 mg, 4.49 mmol), potassium phosphate tribasic (1359 mg, 6.40 mmol), and water (2 mL) was stirred at 80° C. for several hours. 1 N hydrochloric acid (3 mL) was added to the reaction mixture followed by TFA (3 mL) and the reaction was extracted with EtOAc. The organic portion was dried over sodium sulfate, filtered, concentrated, and the product was isolated as a brown solid using preparative reverse-phase HPLC and used in next step without further purification.

Workup

  1. extractionthe reaction was extracted with EtOAc
  2. dry with materialThe organic portion was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customthe product was isolated as a brown solid
  6. customused in next step without further purification

Sources & evidence

ORD record
ord-b2dd61b60b8140bfa25446adb4c386cf
Source dataset
uspto-grants-2009_10
Patent number
US07601844B2

Reaction notes

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