Ethanol → tert-butyl N-[1-(5-bromopyrimidin-2-yl)cyclopropyl]carbamate

HRID 2172958Notes

Reaction equation

HRID 2172958 reaction equation
Cl.[C:2]([O:6][C:7](=[O:15])[NH:8][C:9]1([C:12](=[NH:14])[NH2:13])[CH2:11][CH2:10]1)([CH3:5])([CH3:4])[CH3:3].CN(C)[CH:18]=[C:19]([Br:22])[CH:20]=O.CCO>CO>[C:2]([O:6][C:7](=[O:15])[NH:8][C:9]1([C:12]2[N:13]=[CH:20][C:19]([Br:22])=[CH:18][N:14]=2)[CH2:11][CH2:10]1)([CH3:5])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 702EthanolHCID 573700322-Bromo-3-(dimethylamino)prop-2-enalHCID 67390485Tert-butyl (1-carbamimidoylcyclopropyl)carbamate hcl

Product 1

HCID 67508268tert-butyl N-[1-(5-bromopyrimidin-2-yl)cyclopropyl]carbamate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

(1-Carbamimidoyl-cyclopropyl)-carbamic acid tert-butyl ester hydrochloride (1.0 g, 4.2 mmol) (prepared according to the procedure described in patent application WO 2009/070485 A1) and 3-dimethylamino-2-bromo-propenal (1.1 g, 6.4 mmol) are added to EtOH (2 mL) in a pressure tube. The reaction vessel is capped and the mixture is heated at 80° C. for 24 hours. The mixture is cool to room temperature and methanol (20 mL) is added. The resulting solids are filtered and the filtrate is concentrated in vacuo. The residue is dissolved with CH2Cl2 (50 mL) and the solids are filtered. The filtrate is concentrated and the residue is purified by silica gel chromatography using a gradient of 0-50% EtOAc in hexanes to afford [1-(5-bromo-pyrimidin-2-yl)-cyclopropyl]-carbamic acid tert-butyl ester as a solid.

Workup

  1. customThe reaction vessel is capped
  2. temperatureThe mixture is cool to room temperature
  3. filtrationThe resulting solids are filtered
  4. concentrationthe filtrate is concentrated in vacuo
  5. dissolutionThe residue is dissolved with CH2Cl2 (50 mL)
  6. filtrationthe solids are filtered
  7. concentrationThe filtrate is concentrated
  8. customthe residue is purified by silica gel chromatography

Sources & evidence

ORD record
ord-2308e649d4a947e0b0588140c39161e5
Source dataset
uspto-grants-2015_06
Patent number
US09056858B2

Reaction notes

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