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

HRID 252105Notes

Reaction equation

HRID 252105 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.C(N(C(C)C)CC)(C)C.[Br:25][C:26]1[CH:27]=[N:28][C:29](Cl)=[N:30][CH:31]=1.O>C(#N)C>[Br:25][C:26]1[CH:27]=[N:28][C:29]([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:30][CH:31]=1

Participants

6

Reactant 4

HCID 962WaterHCID 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 83%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
20 °C

Procedure

Add to a solution of (2,4-dichlorobenzyl)-(S)-pyrrolidin-3-ylamine (300 g, 1.22 mol) in acetonitrile (2.25 L) at room temperature diisopropylethylamine (237 g, 1.83 mol) and 5-bromo-2-chloropyrimidine (237 g, 1.23 mol). Reflux for 1 hour. Cool the mixture to 20° C. Add water (45 mL, 2.5 mol) dropwise to give a solid. Stir for 17 h., filter the suspension, and wash the cake with acetonitrile (250 mL), and dry under vacuum at room temperature to give the title compound as a tan solid (377 g, 83%).

Workup

  1. temperatureReflux for 1 hour
  2. filtrationfilter the suspension
  3. washwash the cake with acetonitrile (250 mL)
  4. customdry under vacuum at room temperature

Sources & evidence

ORD record
ord-5f4d06b75d2d4b35a74002692ce5f60d
Source dataset
uspto-grants-2011_01
Patent number
US07868014B2

Reaction notes

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