2-Amino-5-chloropyridine → HCID 21906598, compound

HRID 988624Notes

Reaction equation

HRID 988624 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1.C([Mg]Br)C=C.[C:14]([N:21]1[CH2:26][CH2:25][N:24]([C:27]2[O:32][C:31](=[O:33])[C:30]3[CH:34]=[C:35]([Cl:38])[CH:36]=[CH:37][C:29]=3[N:28]=2)[CH2:23][CH2:22]1)([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15]>O1CCCC1>[C:14]([N:21]1[CH2:22][CH2:23][N:24]([C:27]([NH:28][C:29]2[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][C:30]=2[C:31]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=2)=[O:33])=[O:32])[CH2:25][CH2:26]1)([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15]

Participants

5

Reactant 3

HCID 661742-Amino-5-chloropyridineHCID 21906521HCID 21906521, compoundHCID 178455850HCID 178455850, compound

Product 1

HCID 21906598HCID 21906598, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 2-amino-5-chloropyridine (0.6 g, 4.64 mmol) in tetrahydrofuran (80 mL) at 0° C. under nitrogen was added allylmagnesium bromide (1.0 M in ether, 4.7 mL, 4.7 mmol) dropwise via a syringe. After stirring at 0° C. for 10 min, 2-(4-Boc-1-piperazinyl)-6-chloro-4H-3,1-benzoxazin-4-one (0.8 g, 2.19 mmol) was added. After stirring 15 h at room temperature, the solvent was removed in vacuo. The residue was partitioned between ethyl acetate and saturated aqueous sodium chloride and the layers separated. The organic phase was washed with water, dried (magnesium sulfate), filtered, and concentrated in vacuo to give 0.88 g (82%) of the title compound as a white solid.

Workup

  1. stirringAfter stirring 15 h at room temperature
  2. customthe solvent was removed in vacuo
  3. customThe residue was partitioned between ethyl acetate and saturated aqueous sodium chloride
  4. customthe layers separated
  5. washThe organic phase was washed with water
  6. dry with materialdried (magnesium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-edffc292338f4230ac12977b97531e06
Source dataset
uspto-grants-2003_10
Patent number
US06635657B1

Reaction notes

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