Susquehanna Valley Section

March 2004 Meeting

The three hundred and forty eighth meeting of the Section will be held on Wednesday, March 10, 2004, at Merck Cherokee facility in Danville, Pennsylvania. The lecture will begin promptly at 8:00 pm and the speaker will be Dr. Paul N. Devine, Senior Research Fellow, MRL Process Research.

Dinner: A dinner will be held at Mulberry's (336 Mill Street, Danville, PA 17821) beginning at 6:30 p.m. The dinner entrees are Chicken Marsala, Tenderloin Tips Teriyaki over White Rice, and Broiled Salmon with a Maple Dijon Sauce. Each dinner comes with a choice of soup du jour (cream & broth based), tossed salad (choice of dressing), vegetable (mixed vegetables), potatoes (choice of baked or mashed), dessert (choice of homemade cake or scoop of ice cream), beverage (choose between coffee, decaffeinated coffee, tea, iced tea, soft drinks or milk. The cost of the dinner is $18.50. If you are interested in attending the dinner please RSVP to Pat Burlone (570) 271-2006 by March 8, 2004.

Directions:

To Mulberry's - Take Interstate 80 to Exit 224 (formerly Exit 33, Danville). Turn right at the bottom of the ramp onto Route 54 East. Continue on Route 54 for approximately two miles to the intersection of Route 54 (Continental Boulevard) and Route 11 - there will be a Wendy's restaurant on your left. Turn left at the intersection of Route 54 and 11. Make a right at the next light (Mill Street). Mulberry's is on the left at the corner of Mill and Mulberry streets.

To the Merck Plant (from Mulberry's) - Take Mill Street, through Danville until the road comes to a "T". Make a right at the stop sign, and proceed to the light. Make a left at the light and cross over the bridge. Take the first right after the bridge onto D&H Avenue, and continue straight to the Cherokee Plant. Turn right into the Plant entrance and follow the signs to Visitor Parking.

A Highly Regioselective Synthesis of a 1,2,4-Aminotriazine: Total Synthesis of an a_2,3-selective GABA-A agonist
Paul N. Devine; John Limanto; Donald Gauthier, Jr.; Richard Desmond; Ronald Szumigala, Jr.; Bruce Foster; Skip P. Volante

A convergent and robust synthesis of imidazotriazine 1 has been accomplished and demonstrated on pilot plant scale. The final transformation in the sequence involved an efficient and regioselective Pd-mediated arylation of imidazotriazine 3. The biaryl bromide intermediate 2 was prepared via two regioselective bromination reactions and a Suzuki-Miyaura coupling of two aryl fragments. The imidazotriazine portion of the molecule was synthesized by a regioselective condensation of chloroacetaldehyde with aminotriazine 4. This was in turn accessed by a novel, regioselective condensation of aminoguanidine 6 and the corresponding a,a-dibromohydroxyketone 5. Synthesis of key fragments as well as scope of the methodology will be discussed.

Dr. Devine started his academic career at King's College in Wilkes-Barre (BS). From there he traveled to SUNY-Binghamton where he obtained his Ph. D. After a postdoctoral appointment with A.I. Meyers at Colorado State University, he joined Merck in 1994. Since joining MRL, he has published over 20 patents and papers.