Potassium Phosphate, Tribasic → HCID 86686205, compound

HRID 1021229Notes

Reaction equation

HRID 1021229 reaction equation
I[C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:11][CH:10]([O:12][CH3:13])[CH2:9]2)=[N:6][CH:7]=1.[O:14]=[C:15]1[NH:20][CH2:19][CH2:18][N:17]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:16]1.CN[C@@H]1CCCC[C@H]1NC.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[CH3:13][O:12][CH:10]1[CH2:11][N:8]([C:5]2[N:4]=[CH:3][C:2]([N:20]3[CH2:19][CH2:18][N:17]([C:21]([O:23][C:24]([CH3:26])([CH3:25])[CH3:27])=[O:22])[CH2:16][C:15]3=[O:14])=[CH:7][N:6]=2)[CH2:9]1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 3157178Tert-butyl 3-oxopiperazine-1-carboxylateHCID 68309608HCID 68309608, compound

Product 1

HCID 86686205HCID 86686205, compoundYield 60.9%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

Dioxane (12 ml) was added to a mixture of 5-iodo-2-(3-methoxyazetidin-1-yl)pyrimidine (1.14 g), tert-butyl 3-oxopiperazine-1-carboxylate (941 mg), rel-(1R,2R)-N,N′-dimethyl cyclohexane-1,2-diamine (223 mg), copper iodide (149 mg), and potassium phosphate (2.5 g), followed by stirring at 100° C. overnight. The reaction mixture was cooled to room temperature and then filtered by the addition of CHCl3 and Celite, and the filtrate was concentrated. The obtained residue was purified by basic silica gel column chromatography (EtOAc/hexane) to obtain tert-butyl 4-[2-(3-methoxyazetidin-1-yl)pyrimidin-5-yl]-3-oxopiperazine-1-carboxylate (867 mg).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered by the addition of CHCl3 and Celite
  3. concentrationthe filtrate was concentrated
  4. customThe obtained residue was purified by basic silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-f0db1ee8ce314634a14f11c9b75880b5
Source dataset
uspto-grants-2014_05
Patent number
US08716470B2

Reaction notes

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