1-Phenethylamine, (-)- → HCID 15136845, compound

HRID 2300836Notes

Reaction equation

HRID 2300836 reaction equation
[C:1]1([C@@H:7]([NH2:9])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:10][C:11]1[N:16]=[C:15]([Cl:17])[CH:14]=[C:13]([Cl:18])[N:12]=1>C1COCC1>[C:1]1([C@@H:7]([NH:9][C:11]2[N:16]=[C:15]([Cl:17])[CH:14]=[C:13]([Cl:18])[N:12]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:1]1([C@@H:7]([NH:9][C:15]2[CH:14]=[C:13]([Cl:18])[N:12]=[C:11]([Cl:10])[N:16]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 758181-Phenethylamine, (-)-HCID 773782,4,6-Trichloropyrimidine

Product 2

HCID 15136845HCID 15136845, compoundHCID 86758758HCID 86758758, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (S)-1-phenylethylamine (2.6 mL) in THF (20 mL) at room temperature was added 2,4,6-trichloropyrimidine (1.83 g) dissolved in THF (10 mL) dropwise. The reaction mixture was stirred for 2 h, and then the solid was filtered and washed thoroughly with EtOAc. Combined filtrate was concentrated under reduced pressure, and the crude product was purified by flash chromatography (silica, 1:2), followed by 1:6 EtOAc:hexanes) to give 2-[(S)-1-phenylethylamino]-4,6-dichloropyrimidine (1.2 g) and 4-[(S)-1-phenylethylamino]-2,6-dichloropyrimidine (1.5 g). 2-[(S)-1-phenylethylamino]-4,6-dichloropyrimidine 1H NMR (500 MHz, CDCl3): δ 7.4-7.25 (m, 5H); 6.6 (s, 1H); 5.65 (br s, 1H); 5.2 (m, 1H); 1.58 (d, J=7.1 Hz, 3H). Mass spectrum (CI) 268.2 (M+1). 4-[(S)-1-phenylethylamino]-2,6-dichloropyrimidine 1H NMR (500 MHz, CDCl3): δ 7.41-7.3 (m, 5H); 6.1 (br s, 1H); 5.8 (br s, 1H); 4.6 (br s, 1H); 1.6 (d, J=7.1 Hz, 3H). Mass spectrum (CI) 268.2 (M+1).

Workup

  1. filtrationthe solid was filtered
  2. washwashed thoroughly with EtOAc
  3. concentrationCombined filtrate was concentrated under reduced pressure
  4. customthe crude product was purified by flash chromatography (silica, 1:2)

Sources & evidence

ORD record
ord-74f7e06b79604df3aa7d6c3115dc2323
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Reaction notes

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