Reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[C:12]([Sn](CCCC)(CCCC)CCCC)[CH:11]=[CH:10][C:9]=2[O:27][CH2:28][CH3:29])[N:5]=[C:4]([NH2:30])[N:3]=1.[I-:31].[Na+].[OH-].[Na+].CC1C=CC(S(NCl)(=O)=O)=CC=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(O)C.O.C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[C:12]([I:31])[CH:11]=[CH:10][C:9]=2[O:27][CH2:28][CH3:29])[N:5]=[C:4]([NH2:30])[N:3]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 3
Procedure
To a solution of 4-chloro-6-(5-tributylstannyl-2-ethoxy-phenyl)pyrimidin-2-ylamine (79 mg, 0.13 mmol) in a 3% solution of acetic acid in ethanol (1 ml) was added a solution of sodium iodide (24 mg, 0.16 mmol) in a 0.1 M aqueous sodium hydroxide solution (0.2 ml) followed by a solution of chloramine-T (15.0 mg, 0.065 mmol) in water (0.15 ml). The orange solution was stirred at room temperature for 1 hour, treated with saturated aqueous sodium thiosulfate solution (0.3 ml), and extracted with ethyl acetate (2×1 ml). The combined extracts were concentrated under reduced pressure. The residue was purified by preparative TLC eluting with 20% ethyl acetate-hexane to provide 4-chloro-6-(5-iodo-2-ethoxy-phenyl)pyrimidin-2-ylamine (39 mg, 71% yield) as a white powder. 1H NMR (CDCl3) δ 8.24 (d, J=2.3 Hz, 1H), 7.67 (dd, J=2.3, 8.70 Hz, 1H), 7.38 (d, J=8.70 Hz, 2H), s, 1H), 6.76 (d, J=8.70 Hz, 1H), 5.23 (s, 1H), 4.13 (q, J=7.0 Hz, 2H), 1.47 (t, J=7.0 Hz, 3H).
Workup
- extractionextracted with ethyl acetate (2×1 ml)
- concentrationThe combined extracts were concentrated under reduced pressure
- customThe residue was purified by preparative TLC
- washeluting with 20% ethyl acetate-hexane
Sources & evidence
- ORD record
- ord-375456bb216c4397905569f9f9311fa7
- Source dataset
- uspto-grants-2008_09
- Patent number
- US07419984B2
Linked notes
Loading…