Diisopropylethylamine → 5-bromo-N-(2-(4-fluorophenyl)-2-methylpropyl)pyrimidin-2-amine

HRID 1474089Notes

Reaction equation

Cl[C:2]1C=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[F:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([CH3:20])([CH3:19])[CH2:17][NH2:18])=[CH:12][CH:11]=1.CC[N:23](C(C)C)C(C)C>C1(C)C=CC=CC=1>[Br:8][C:5]1[CH:4]=[N:3][C:2]([NH:18][CH2:17][C:16]([C:13]2[CH:12]=[CH:11][C:10]([F:9])=[CH:15][CH:14]=2)([CH3:20])[CH3:19])=[N:23][CH:6]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a 20 dram vial was added 2-chloro-5-bromopyridine (440 mg, 2.3 mmol, 1.1 equiv), 2-(4-fluorophenyl)-2-methylpropan-1-amine (350 mg, 2.1 mmol, 1.0 equiv), DIPEA (1.0 mL, 5.7 mmol, 2.7 equiv), and toluene (5 mL). The vial was heated in an oil bath to 80° C. and stirred for 12 h, concentrated, and purified by silica gel column chromatography (0-30% EtOAc/hexanes) to give 270 mg (40%) of 5-bromo-N-(2-(4-fluorophenyl)-2-methylpropyl)pyrimidin-2-amine as a white solid.

Workup

concentrationconcentrated
custompurified by silica gel column chromatography (0-30% EtOAc/hexanes)

Sources & evidence

ORD record: ord-7d951fdf4e6a427ba56f1da541a73439
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018223B2

Reaction notes

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