Diisopropylethylamine → tert-butyl N-[2-[(5-bromo-2-chloro-pyrimidin-4-yl)amino]ethyl]carbamate

HRID 2362273Notes

Reaction equation

HRID 2362273 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.CCN(C(C)C)C(C)C.[C:19]([O:23][C:24]([NH:26][CH2:27][CH2:28][NH2:29])=[O:25])([CH3:22])([CH3:21])[CH3:20]>C(O)C>[Br:1][C:2]1[C:3]([NH:29][CH2:28][CH2:27][NH:26][C:24](=[O:25])[O:23][C:19]([CH3:21])([CH3:20])[CH3:22])=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 187201N-BOC-ethylenediamineHCID 2899735-Bromo-2,4-dichloropyrimidine

Product 1

HCID 86695590tert-butyl N-[2-[(5-bromo-2-chloro-pyrimidin-4-yl)amino]ethyl]carbamate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 5-bromo-2,4-dichloropyrimidine 3.2 g (0.0135 mole) in ethanol 80 mL was added Hunig's base 3.0 mL followed by the addition of a solution of N-(tert-butoxy carbonyl)-1,2-diaminoethane 2.5 g (0.0156 mole) in 20 mL ethanol. The contents were stirred overnight for 20 hrs. The solvent was evaporated under vacuum. Ethyl acetate (200 mL) and water (100 mL) was added and the layers separated. The organic layer was dried with magnesium sulfate and then concentrated under vacuum. Column chromatography on silica gel using hexane/ethyl acetate (0-60%) afforded tert-butyl N-[2-[(5-bromo-2-chloro-pyrimidin-4-yl)amino]ethyl]carbamate. 1HNMR (d6-DMSO) 8.21 (s, 1H), 7.62 (brs, 1H), 7.27 (brs, 1H), 3.39 (m, 2H), 3.12 (m, 2H), 1.34 (s, 9H). LCMS (ESI) 351 (M+H)

Workup

  1. customThe solvent was evaporated under vacuum
  2. additionEthyl acetate (200 mL) and water (100 mL) was added
  3. customthe layers separated
  4. dry with materialThe organic layer was dried with magnesium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-e9642fdfd84946c98e1b7ab844fb53f6
Source dataset
uspto-grants-2014_04
Patent number
US08691830B2

Reaction notes

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