Triethylamine → (S)-4,6-Dichloro-N-[1-(4-fluorophenyl)ethyl]pyrimidin-2-amine

HRID 1187668Notes

Reaction equation

HRID 1187668 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[N:3]=1.C(N(CC)CC)C.[F:17][C:18]1[CH:23]=[CH:22][C:21]([C@@H:24]([NH2:26])[CH3:25])=[CH:20][CH:19]=1>O1CCCC1>[Cl:9][C:4]1[CH:5]=[C:6]([Cl:8])[N:7]=[C:2]([NH:26][C@H:24]([C:21]2[CH:22]=[CH:23][C:18]([F:17])=[CH:19][CH:20]=2)[CH3:25])[N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 773782,4,6-TrichloropyrimidineHCID 2779063(S)-1-(4-Fluorophenyl)-ethylamine

Product 1

HCID 86659372(S)-4,6-Dichloro-N-[1-(4-fluorophenyl)ethyl]pyrimidin-2-amineYield 47.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2.4 g of 2,4,6-trichloropyrimidine was dissolved in 24 ml of tetrahydrofuran, and 2.0 ml of triethylamine was added at room temperature, and a solution of 2.0 g of (S)-(−)-1-(4-fluorophenyl)ethylamine in 12 mL of tetrahydrofuran was added dropwise, and then the mixture was stirred at room temperature for 9.5 hours. The reaction mixture was filtrated to remove precipitates, and then the filtrate was concentrated under reduced pressure. The residue was purified with silica gel column chromatography to obtain 1.77 g of the objective compound.

Workup

  1. filtrationThe reaction mixture was filtrated
  2. customto remove
  3. customprecipitates
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified with silica gel column chromatography

Sources & evidence

ORD record
ord-b0a243fcb7434d3e8391fa8649ee76fb
Source dataset
uspto-grants-2014_03
Patent number
US08673891B2

Reaction notes

Loading…