1-Phenethylamine, (-)- → HCID 59924636, compound

HRID 2300792Notes

Reaction equation

HRID 2300792 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[CH:4][N:3]=1.[C:9]1([C@@H:15]([NH2:17])[CH3:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C1COCC1>[C:9]1([C@@H:15]([NH:17][C:2]2[N:7]=[C:6]([Cl:8])[CH:5]=[CH:4][N:3]=2)[CH3:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 758181-Phenethylamine, (-)-HCID 775312,4-Dichloropyrimidine

Product 1

HCID 59924636HCID 59924636, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2,4-dichloropyrimidine (500 mg, 3.38 mmol, 1 eq) in THF (15 mL) was added (S)-1-phenylethylamine. After 48 h the precipitate was filtered off and washed with THF. The THF was removed under reduced pressure and the material was purified by silica gel chromatography (eluted with 4:1 hexanes/acetone) to give 167 mg of the desired product. [Note: 2-[(S)-1-phenylethylamino]-4-chloropyrimidine is the faster but minor regioisomer. The major, slower product is 2-chloro-4-[(S)-1-phenylethylamino]pyrimidine.]

Workup

  1. filtrationAfter 48 h the precipitate was filtered off
  2. washwashed with THF
  3. customThe THF was removed under reduced pressure
  4. customthe material was purified by silica gel chromatography (eluted with 4:1 hexanes/acetone)

Sources & evidence

ORD record
ord-192430f84bef4ae8ac957ae2e266ba68
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Reaction notes

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