Phosphorus oxychloride → HCID 58382461, compound
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[CH:7]=[C:6]2[C:13]1[N:28]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[C:16]2=[N:17][CH:18]=[C:19]([CH2:21][NH:22][C:23](=O)[N:24]([CH3:26])[CH3:25])[N:20]=[C:15]2[CH:14]=1.O=P(Cl)(Cl)Cl>ClCCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[CH:7]=[C:6]2[C:13]1[N:28]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:35])([CH3:36])[CH3:34])[C:16]2[N:17]=[CH:18][C:19]3[N:20]([C:23]([N:24]([CH3:26])[CH3:25])=[N:22][CH:21]=3)[C:15]=2[CH:14]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 85 °C
Procedure
A flask was charged with 3-((6-(5-methoxy-1-methyl-1H-indol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)methyl)-1,1-dimethylurea (0.114 g, 0.224 mmol, Preparation #X.1) and DCE (5 mL). A solution of POCl3 (0.063 mL, 0.672 mmol) in DCE (2 mL) was added and mixture was heated to about 85° C. for about 3 h. The mixture was concentrated under reduced pressure and then diluted with EtOAc (15 mL) and washed with saturated aqueous NaCl (10 mL). The organic layer was dried with anhydrous MgSO4, filtered and concentrated in vacuo. The material was purified using silica gel chromatography with an elution gradient of 0 to 100% EtOAc/heptane to give 7-(5-methoxy-1-methyl-1H-indol-3-yl)-N,N-dimethyl-6-((2-(trimethylsilyl)ethoxy)methyl)-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-amine (0.47 g, 43%): LC/MS (Table 2, Method b) Rt=3.14 min; MS m/z: 491 (M+H)+.