title: Reversible carboxamide-mediated internal activation at C(6) of 2-chloro-4-anilino-1H-pyrrolo[2,3-d]pyrimidines.
abstract: A synthetic route to bisanilino-1H-pyrrolo[2,3-d]pyrimidines has been discovered, wherein the C(6)-chloride reactivity is necessarily enhanced via reversible acid-catalyzed internal activation of the pyrimidine ring by a C(1')-carboxamide moiety. Subsequent selective nucleophilic displacements at C(6) and C(1') constitute a one-pot tandem protocol for the rapid assembly of bisanilino-1H-pyrrolo[2,3-d]pyrimidines.
authors.affiliation: GlaxoSmithKline, Oncology R&D, 5 Moore Drive, Research Triangle Park, North Carolina 27709, USA.
authors.forename: Stanley D
authors.initials: SD
authors.lastname: Chamberlain
authors.forename: Roseanne M
authors.initials: RM
authors.lastname: Gerding
authors.forename: Huangshu
authors.initials: H
authors.lastname: Lei
authors.forename: Ganesh
authors.initials: G
authors.lastname: Moorthy
authors.forename: Samarjit
authors.initials: S
authors.lastname: Patnaik
authors.forename: Anikó M
authors.initials: AM
authors.lastname: Redman
authors.forename: Kirk L
authors.initials: KL
authors.lastname: Stevens
authors.forename: Joseph W
authors.initials: JW
authors.lastname: Wilson
authors.forename: Bin
authors.initials: B
authors.lastname: Yang
authors.forename: J Brad
authors.initials: JB
authors.lastname: Shotwell
mesh_terms: D000577:Amides / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods*; D002712:Chlorides / Q000737:chemistry; D015195:Drug Design; D008956:Models, Chemical; D011743:Pyrimidines / Q000737:chemistry*; D011758:Pyrroles / Q000737:chemistry*
chemical_list: C538706:4,6-bis-anilino-1H-pyrrolo(2,3-d)pyrimidine; D000577:Amides; D002712:Chlorides; D011743:Pyrimidines; D011758:Pyrroles; D002244:Carbon