7-bromo-3-methyl-1,2,3,4-tetrahydroisoquinoline

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: This compound was prepared by using procedures analogous to those described for the synthesis of Example 1 starting from 7-bromo-3-methyl-1,2,3,4-tetrahydroisoquinoline and 2-Amino-4,6-dichloropyrimidine (Alfa Aesar, Cat. No. A11330). LCMS (M+H)+: m/z=353.0. This compound was prepared

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Iodotrimethylsilane (0.982 mL, 0.00690 mol, Aldrich, Cat. No. 195529) was added to a solution of methyl 7-bromo-3-methyl-3,4-dihydroisoquinoline-2(1H)-carboxylate (490 mg, 0.0017 mol) in methylene chloride (10 mL) and the reaction was stirred at 50° C. for 2 h. The reaction was cooled to r.t. and anhydrous methanol (2 mL) was added. The reaction mixture was stirred for additional 5 min, and the volatiles were removed under reduced pressure. The residue was treated with diethyl ether and filtered. The solid was washed with ether, dried under vacuum to provide the desired compound which was directly used in the next step reaction without further purification. LCMS (M+H)+: m/z=226.2. The reaction was cooled to r.t. The reaction mixture was stirred for additional 5 min the volatiles were removed under reduced pressure The residue was treated with diethyl ether filtered The solid was washed with ether dried under vacuum