Diisopropylethylamine → (3S)-1-(5-bromopyrimidin-2-yl)-N-[(2,4-dichlorophenyl)methyl]pyrrolidin-3-amine

HRID 252102Notes

Reaction equation

HRID 252102 reaction equation
[Cl:1][C:2]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:3]=1[CH2:4][NH:5][C@H:6]1[CH2:10][CH2:9][NH:8][CH2:7]1.Cl[C:17]1[N:22]=[CH:21][C:20]([Br:23])=[CH:19][N:18]=1.C(N(C(C)C)CC)(C)C>C(#N)C>[Br:23][C:20]1[CH:19]=[N:18][C:17]([N:8]2[CH2:9][CH2:10][C@H:6]([NH:5][CH2:4][C:3]3[CH:11]=[CH:12][C:13]([Cl:15])=[CH:14][C:2]=3[Cl:1])[CH2:7]2)=[N:22][CH:21]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 6066655-Bromo-2-chloropyrimidineHCID 66569981(S)-N-(2,4-Dichlorobenzyl)pyrrolidin-3-amine

Product 1

HCID 11503055(3S)-1-(5-bromopyrimidin-2-yl)-N-[(2,4-dichlorophenyl)methyl]pyrrolidin-3-amineYield 87.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Stir a mixture of (S)-(2,4-dichlorobenzyl)-pyrrolidin-3-ylamine (313 mg, 1.28 mmol), 2-chloro-5-bromopyrimidine (248 mg, 1.28 mmol) and diisopropylethylamine (335 μL, 1.91 mmol) in acetonitrile (2 mL) at 80° C. overnight. Concentrate and chromatograph on SCX-2 column to give the title compound (450 mg, 87%). Form the hydrochloride by essentially the procedure in Example 1 to give 1H NMR (400 MHz, MeOH-d4) δ 8.41 (2H, s), 7.62-7.67 (2H, m), 7.49 (1H, dd, J=8.31, 1.96 Hz), 4.46 (2H, d, J=5.62 Hz), 4.16 (1H, m), 3.99-4.05 (1H, m), 3.79-3.86 (2H, m), 3.65 (1H, m), 2.60 (1H, m), 2.28-2.37 (1H, m), MS (ES): m/z=402 [M+].

Workup

  1. concentrationConcentrate

Sources & evidence

ORD record
ord-d2cf04c76e67405cb590d3ef79703f06
Source dataset
uspto-grants-2011_01
Patent number
US07868014B2

Reaction notes

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