Chloroform → HCID 58405679, compound

HRID 44849

Reaction equation

HRID 44849 reaction equation
Br[C:2]1[N:3]([C:7]2[N:16]=[CH:15][C:14]3[N:13]([CH3:17])[C:12](=[O:18])[C@@H:11]([CH2:19][CH3:20])[N:10]([CH:21]4[CH2:25][CH2:24][CH2:23][CH2:22]4)[C:9]=3[N:8]=2)[CH:4]=[CH:5][N:6]=1.[NH:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1.C(Cl)(Cl)Cl.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[K+].[K+]>CC(O)(C)C.CCOC(C)=O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH:21]1([N:10]2[C:9]3[N:8]=[C:7]([N:3]4[CH:4]=[CH:5][N:6]=[C:2]4[N:26]4[CH2:30][CH2:29][CH2:28][CH2:27]4)[N:16]=[CH:15][C:14]=3[N:13]([CH3:17])[C:12](=[O:18])[C@H:11]2[CH2:19][CH3:20])[CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

9

Reactant 5

HCID 6212ChloroformHCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 634876Binap, (A+-)-HCID 58405307(R)-2-(2-bromo-1H-imidazol-1-yl)-8-cyclopentyl-7-ethyl-5-methyl-7,8-dihydropteridin-6(5H)-one

Product 1

HCID 58405679HCID 58405679, compoundYield 38.3%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6386tert-ButanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

(R)-2-(2-bromo-1H-imidazol-1-yl)-8-cyclopentyl-7-ethyl-5-methyl-7,8-dihydropteridin-6(5H)-one (Example 65, 150 mg, 0.37 mmol), pyrrolidine (52 mg, 0.74 mmol), Pd2dba3.CHCl3 (76 mg, 0.074 mmol), BINAP (69 mg, 0.11 mmol) and K2CO3 (153 mg, 1.11 mmol) were dissolved in 1 mL of degassed t-BuOH and the resulting solution was heated at 130° C. for 18 h. The reaction mixture was diluted with EtOAc and washed with brine. The organic extracts were dried with Na2SO4, filtered and evaporated, and the residue was purified by preparative HPLC to give the title compound (56 mg). LCMS: 396.2 m/z (M+H)+; ret. Time: 2.76 min (Analytical Method A).

Workup

  1. washwashed with brine
  2. dry with materialThe organic extracts were dried with Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-b4594beaad694721a1b74d411a3f9d6f
Source dataset
uspto-grants-2013_09
Patent number
US08541418B2

Linked notes

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