1-Phenethylamine, (-)- → HCID 9926914, compound

HRID 2300719Notes

Reaction equation

HRID 2300719 reaction equation
CS([C:5]1[N:10]=[C:9]([N:11]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[N:13]=[CH:12]2)[CH:8]=[CH:7][N:6]=1)(=O)=O.[C:20]1([C@@H:26]([NH2:28])[CH3:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[C:20]1([C@@H:26]([NH:28][C:5]2[N:10]=[C:9]([N:11]3[C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=4[N:13]=[CH:12]3)[CH:8]=[CH:7][N:6]=2)[CH3:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

3

Reactant 2

HCID 758181-Phenethylamine, (-)-HCID 155496402-Methanesulfonyl-4-[benzimidazol-1-yl]pyrimidine

Product 1

HCID 9926914HCID 9926914, compoundYield 57%

Procedure

A solution of 2-methanesulfonyl-4-[benzimidazol-1-yl]pyrimidine (0.203 g, 0.74 mmol) and (S)-1-phenylethylamine (0.15 mL, 1.16 mmol) in 2 mL of xylenes was heated to 100° C. After 8 h, the reaction mixture was concentrated and purified by chromatography (silica, 1:1 hexanes: EtOAc, then 1:1 CH2Cl2: EtOAc) to give 0.133 g of the title compound. 1H NMR (500 MHz, CDCl3): δ 8.49 (br s, 1H); 8.39 (d, J=5.5 Hz, 1H); 7.83 (d, J=8.0 Hz, 1H); 7.3-7.5 (m, 8H); 6.79 (d, J=5.5 Hz, 1H); 5.75 (br s, 1H); 5.21 (br s, 1H); 1.65 (d, J=6.9 Hz, 3H).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. custompurified by chromatography (silica, 1:1 hexanes

Sources & evidence

ORD record
ord-ce6d638a17b248a686b624de76822340
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Reaction notes

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