Water → HCID 66940125, compound

HRID 1157167Notes

Reaction equation

HRID 1157167 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][C@@H:12]2[CH2:14][C@H:9]1[CH2:10][N:11]2[C:15]1[N:20]=[CH:19][C:18](Br)=[CH:17][N:16]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:22]([Sn](CCCC)(CCCC)C=C)[CH2:23]CC.C(OCC)(=O)C.O>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][C@@H:12]2[CH2:14][C@H:9]1[CH2:10][N:11]2[C:15]1[N:20]=[CH:19][C:18]([CH:22]=[CH2:23])=[CH:17][N:16]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 81998TributylvinyltinHCID 581904111,1-Dimethylethyl (1S,4S)-5-(5-bromo-2-pyrimidinyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

Product 1

HCID 66940125HCID 66940125, compoundYield 35.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

(S,S)-5-(5-Bromo-pyrimidin-2-yl)-2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester (177 mg, 0.5 mmol), tributyl vinyl tin (634 mg, 2 mmol) and Cl2Pd(dppf)CH2Cl2 (60 mg) was mixed in DMF (3 mL). The mixture was heated at 90° C. over 3 days. The cooled down reaction was participate between ethyl acetate (50 mL) and H2O (10 mL). The organic layer washed with H2O (10 mL), brine (10 mL), dried (MgSO4) and filtered. The conc. filtrate was purified on silica gel column eluting with 33% to 50% ethyl acetate/hexanes to yield the title compound as a white solid (54 mg). MS (303, MH).

Workup

  1. temperatureThe cooled down reaction
  2. washThe organic layer washed with H2O (10 mL), brine (10 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customThe conc. filtrate was purified on silica gel column
  6. washeluting with 33% to 50% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-1eefb35d944f40afb6b8183867e79a9a
Source dataset
uspto-grants-2010_10
Patent number
US07807672B2

Reaction notes

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