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

HRID 1819464Notes

Reaction equation

[Br:1][C:2]1[C:3](Cl)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.Cl.[C:11]([O:15][C:16](=[O:26])[NH:17][C@H:18]1[CH2:23][CH2:22][C@H:21]([CH2:24][NH2:25])[CH2:20][CH2:19]1)([CH3:14])([CH3:13])[CH3:12].CCN(C(C)C)C(C)C>CC(N(C)C)=O>[C:11]([O:15][C:16](=[O:26])[NH:17][CH:18]1[CH2:19][CH2:20][CH:21]([CH2:24][NH:25][C:3]2[C:2]([Br:1])=[CH:7][N:6]=[C:5]([Cl:8])[N:4]=2)[CH2:22][CH2:23]1)([CH3:14])([CH3:12])[CH3:13]

Participants

Conditions

Temperature: 25 °C

Procedure

5-Bromo-2,4-dichloropyrimidine (1.1 g, 4.83 mmol) was dissolved in DMA (25 mL). To this solution was added tert-butyl-trans-4-aminomethylcyclohexylcarbamate hydrochloride (1.54 g, 5.80 mmol), followed by DIEA (1.98 mL, 11.4 mmol). The reaction was stirred at 25° C. for 18 h. The reaction was worked up by removal of the volatiles in vacuo. The crude was purified via flash chromatography (SiO2, 10-25% EtOAc-Hexanes) to afford 1.32 g (65%) of {4-[(5-bromo-2-chloro-pyrimidin-4-ylamino)-methyl]-cyclohexyl}-carbamic acid tert-butyl ester.

Workup

customThe reaction was worked up by removal of the volatiles in vacuo
customThe crude was purified via flash chromatography (SiO2, 10-25% EtOAc-Hexanes)

Sources & evidence

ORD record: ord-029887537cb445cfbbbc7213bf61d800
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07601714B2

Reaction notes

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