Dimethylamine → tert-Butyl N-[1-(pyrimidin-2-yl)cyclopropyl]carbamate

HRID 1040472Notes

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:19]([CH:21]=[CH2:22])=O)C.CNC>CCO>[C:2]([O:6][C:7](=[O:15])[NH:8][C:9]1([C:12]2[N:13]=[CH:22][CH:21]=[CH:19][N:14]=2)[CH2:11][CH2:10]1)([CH3:5])([CH3:3])[CH3:4]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of (1-Carbamimidoyl-cyclopropyl)-carbamic acid tert-butyl ester hydrochloride (3.62 g, 15.4 mmol) in anhydrous EtOH (62 mL) was added dimethylaminoacrolein (3.6 mL, 36. mmol) and dimethylamine (2 M in THF, 10. mL, 20. mmol). The reaction was heated at 70° C. for 18 h. The EtOH was removed in vacuo and the residue was dissolved in EtOAc (150 mL) and washed with water (3×100 ml). The organic phase was dried with Na2SO4 and concentrated to give a red oil. The product was crystallized from the oil using warm hexanes (30 mL) and the light orange solids were collected by filtration. The filtrate was re-processed in the same manner two additional times. In total 2.23 g of the title compound was isolated as a light orange powder, m/z 236.40 [M+1]+

Workup

customThe EtOH was removed in vacuo
dissolutionthe residue was dissolved in EtOAc (150 mL)
washwashed with water (3×100 ml)
dry with materialThe organic phase was dried with Na2SO4
concentrationconcentrated
customto give a red oil
customThe product was crystallized from the oil
temperatureusing warm hexanes (30 mL)
filtrationthe light orange solids were collected by filtration

Sources & evidence

ORD record: ord-1fd5399ed6754807b3db33945b1793f7
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08552205B2

Reaction notes

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