Water → HCID 66940125, compound

HRID 1038028Notes

Reaction equation

HRID 1038028 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 was 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 was 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-0b363c07576d4cf9b6ea41511d91155f
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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