5-Bromo-2-chloropyrimidine → HCID 68781024, compound

HRID 2264426Notes

Reaction equation

HRID 2264426 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5](Cl)=[N:6][CH:7]=1.[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][CH:19]([NH2:22])[CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10]>C(#N)C>[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][CH:19]([NH:22][C:5]2[N:4]=[CH:3][C:2]([Br:1])=[CH:7][N:6]=2)[CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:10])[CH3:11]

Participants

4

Reactant 2

HCID 6066655-Bromo-2-chloropyrimidineHCID 12682914-Amino-1-Boc-piperidine

Product 1

HCID 68781024HCID 68781024, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 5-bromo-2-chloro-pyrimidine (1.67 g, 8.63 mmol, 1.0 equiv; commercially available) and 4-amino-piperidine-1-carboxylic acid tert-butyl ester (2.08 g, 10.36 mmol, 1.2 equiv; commercially available) in acetonitrile (10 mL) was heated by microwave irradiation to 120° C. for 40 min. The organic phase was concentrated under reduced pressure and the residue purified by silica column chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of heptane/ethyl acetate providing 1.48 g (48%) of the title compound. MS (ISP): 357.3 [M+H]+.

Workup

  1. concentrationThe organic phase was concentrated under reduced pressure
  2. customthe residue purified by silica column chromatography
  3. washeluting with a gradient of heptane/ethyl acetate providing 1.48 g (48%) of the title compound

Sources & evidence

ORD record
ord-7bab793d2c8d467d9e61b11ff18403fe
Source dataset
uspto-grants-2010_12
Patent number
US07855194B2

Reaction notes

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