Diisopropylethylamine → {4-[(2,5-Dichloro-pyrimidin-4-ylamino)-methyl]-cyclohexyl}-carbamic acid tert-butyl ester

To a solution of the above 5-chloro-2,4-dichloropyrimidine (73 mg, 0.4 mmol) in EtOH (2 mL) were added tert-butyl trans-4-aminomethylcyclohexylcarbamate (100 mg, 0.44 mmol) and DIPEA (77 μL, 0.44 mmol). The reaction mixture was heated at 40° C. for 1 h. The reaction mixture was concentrated in vacuo and the resulting residue was diluted with EtOAc. The solution was washed with brine. The aqueous layer was re-extracted with EtOAc (×2). The combined organic phase was dried over anhydrous Na2SO4 and concentrated in vacuo to yield 148 mg (99%) of {4-[(2,5-dichloro-pyrimidin-4-ylamino)-methyl]-cyclohexyl}-carbamic acid tert-butyl ester.

1. concentrationThe reaction mixture was concentrated in vacuo
2. additionthe resulting residue was diluted with EtOAc
3. washThe solution was washed with brine
4. extractionThe aqueous layer was re-extracted with EtOAc (×2)
5. dry with materialThe combined organic phase was dried over anhydrous Na2SO4
6. concentrationconcentrated in vacuo

ORD record

ord-e511ebfdf1c741c681385cae4acb4522

Source dataset

uspto-grants-2009_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07601714B2