Methanol → 3,3-bis(4-fluorophenyl)-N-(2-(pyrimidin-2-yl)ethyl)propan-1-amine

HRID 2190322Notes

Reaction equation

C([N:8]([CH2:26][CH2:27][C:28]1[N:33]=[CH:32][CH:31]=[CH:30][N:29]=1)[CH2:9][CH2:10][CH:11]([C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)[C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)C1C=CC=CC=1.C([O-])=O.[NH4+].CO>C(Cl)Cl.[Pd]>[F:18][C:15]1[CH:16]=[CH:17][C:12]([CH:11]([C:19]2[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=2)[CH2:10][CH2:9][NH:8][CH2:26][CH2:27][C:28]2[N:29]=[CH:30][CH:31]=[CH:32][N:33]=2)=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a mixture of N-benzyl-3,3-bis(4-fluorophenyl)-N-(2-(pyrimidin-2-yl)ethyl)propan-1-amine (1.23 g, 2.77 mmol), ammonium formate (0.985 g, 15.6 mmol), and palladium (10% wt on carbon) (0.382 g, 3.59 mmol) was added MeOH (10 mL). The reaction mixture was heated to 50° C. for 1 h, diluted with DCM, filtered and partially concentrated, diluted with EtOAc, washed with brine (1×), dried over MgSO4, filtered, and concentrated. Purification by flash column chromatography on silica gel (eluted with 5% to 10% MeOH (2 M NH3) in DCM) gave 3,3-bis(4-fluorophenyl)-N-(2-(pyrimidin-2-yl)ethyl)propan-1-amine.

Workup

filtrationfiltered
concentrationpartially concentrated
additiondiluted with EtOAc
washwashed with brine (1×)
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated
customPurification by flash column chromatography on silica gel (eluted with 5% to 10% MeOH (2 M NH3) in DCM)

Sources & evidence

ORD record: ord-ff3355c01cfb404ea2c12091966c32a1
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324396B2

Reaction notes

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