Diisopropylethylamine → (5-Bromo-pyrimidin-2-yl)-(5'-isopropyl-2'-methoxy-4-trifluoromethyl-biphenyl-2-ylmethyl)-amine

HRID 604153Notes

Reaction equation

[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([O:22][CH3:23])=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:11]=2[CH2:20][NH2:21])[CH:9]=1)([CH3:3])[CH3:2].[Br:24][C:25]1[CH:26]=[N:27][C:28](Cl)=[N:29][CH:30]=1.C(N(CC)C(C)C)(C)C>O1CCOCC1>[Br:24][C:25]1[CH:26]=[N:27][C:28]([NH:21][CH2:20][C:11]2[CH:12]=[C:13]([C:16]([F:17])([F:18])[F:19])[CH:14]=[CH:15][C:10]=2[C:8]2[CH:9]=[C:4]([CH:1]([CH3:3])[CH3:2])[CH:5]=[CH:6][C:7]=2[O:22][CH3:23])=[N:29][CH:30]=1

Participants

Conditions

Temperature: 100 °C

Procedure

C-(5′-isopropyl-2′-methoxy-4-trifluoromethyl-biphenyl-2-yl)-methylamine (3.47 g) is dissolved in dioxane (50 ml), and thereto are added 5-bromo-2-chloropyrimidine (5.30 g) and N,N-diisopropylethylamine (5.74 ml) and the mixture is stirred at 100° C. for 2 hours and a half. The reaction solution is allowed to cool to room temperature, and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=50:1→22:3) to give (5-bromo-pyrimidin-2-yl)-(5′-isopropyl-2′-methoxy-4-trifluoromethyl-biphenyl-2-ylmethyl)-amine (4.82 g). MS (m/z): 482/480 [M+H]+

Workup

temperatureto cool to room temperature
concentrationconcentrated under reduced pressure
customThe resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=50:1→22:3)

Sources & evidence

ORD record: ord-cf3972c6e5ff4c768558029dbd03728c
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07906517B2

Reaction notes

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