Ammonia → 1H-Pyrazolo(3,4-d)pyrimidine

HRID 24970

Reaktionsgleichung

Reaktionsgleichung von HRID 24970
CC(OP(COCCCl)(=O)OC(C)C)C.CS[C:18]1[N:23]=[C:22](SC)[N:21]=[C:20]2[NH:26][N:27]=[CH:28][C:19]=12.C1CCN2C(=NCCC2)CC1.[OH-].[Na+].ClC1C=CC=C(C(OO)=O)C=1.CS(C)(=O)=O.N.Br[Si](C)(C)C>[Pd]>[NH:26]1[C:20]2=[N:21][CH:22]=[N:23][CH:18]=[C:19]2[CH:28]=[N:27]1

Komponenten

10

Edukt 8

HCID 222AmmoniaHCID 6213Dimethyl SulfoneHCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 76113BromotrimethylsilaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2236954,6-Bis(methylthio)-1H-pyrazolo[3,4-d]pyrimidineHCID 10587339Di-(2-propyl)-2-chloroethoxymethylphosphonate

Produkt 1

HCID 674991H-Pyrazolo(3,4-d)pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23938PalladiumKatalysator

Versuchsvorschrift

Di-(2-propyl)-2-chloroethoxymethylphosphonate is reacted with 4,6-bismethylmercapto-pyrazolo[3,4-d]pyrimidine (Tetrahedron, 1967, 23: 891) in the presence of DBU to effect attachment at the pyrazole ring nitrogen(s). Displacement of the 4-methymercapto functionality and concommitant monoester hydrolysis is then effected using aqueous sodium hydroxide. Displacement of the remaining 6-methymercapto group is accomplished (after initial oxidation with m-chloroperbenzoic acid to the intermediate methy sulfone) using methanolic ammonia. Bromination at the 3-position is performed according to the procedure described in J. Med. Chem. 1984, 27: 1026-30. Displacement of the 3-bromo group with Fmoc-protected propargylamine is effected using the palladium(0) catalyst described above. The remaining phosphate ester is then deprotected using bromotrimethylsilane. Pyrophosphorylation, deprotection and dye coupling are then performed as described above to yield the fluorescently labeled PME-G-pp analog (pyrazolo[3,4-d]pyrimidine analog).

Quellen und Nachweise

ORD-Eintrag
ord-f651969384424f18a67bd67ddd5a9807
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858393B1

Verknüpfte Notizen

Wird geladen…