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

HRID 2043389Notes

Reaction equation

HRID 2043389 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-00b20d17c6734e0f8b1e554fbbaad559
Source dataset
uspto-grants-2013_11
Patent number
US08586591B2

Reaction notes

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