Hydrogen Peroxide → 4-(2-amino-4-chloro-7-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)but-3-ynyl di-tert-butyl phosphate

HRID 417880

Reaktionsgleichung

Reaktionsgleichung von HRID 417880
[NH2:1][C:2]1[N:3]=[C:4]([Cl:27])[C:5]2[C:10]([C:11]#[C:12][CH2:13][CH2:14][OH:15])=[CH:9][N:8]([CH2:16][C:17]3[C:22]([CH3:23])=[C:21]([O:24][CH3:25])[C:20]([CH3:26])=[CH:19][N:18]=3)[C:6]=2[N:7]=1.N1C=NN=N1.C(N(C(C)C)[P:37]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])[O:38][C:39]([CH3:42])([CH3:41])[CH3:40])(C)C.OO.C([O-])(O)=[O:54].[Na+]>C1COCC1.CCOC(C)=O>[P:37]([O:38][C:39]([CH3:40])([CH3:41])[CH3:42])([O:43][C:44]([CH3:45])([CH3:46])[CH3:47])([O:15][CH2:14][CH2:13][C:12]#[C:11][C:10]1[C:5]2[C:4]([Cl:27])=[N:3][C:2]([NH2:1])=[N:7][C:6]=2[N:8]([CH2:16][C:17]2[C:22]([CH3:23])=[C:21]([O:24][CH3:25])[C:20]([CH3:26])=[CH:19][N:18]=2)[CH:9]=1)=[O:54]

Komponenten

8

Edukt 5

HCID 784Hydrogen PeroxideHCID 516892Sodium BicarbonateHCID 853005Di-tert-butyl N,N-DiisopropylphosphoramiditeHCID 119505104-[2-Amino-4-chloro-7-(4-methoxy-3,5-dimethyl-pyridin-2-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]-but-3-yn-1-olHCID 178418441HCID 178418441, Verbindung

Produkt 1

HCID 577138544-(2-amino-4-chloro-7-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)but-3-ynyl di-tert-butyl phosphate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 4-[2-Amino-4-chloro-7-(4-methoxy-3,5-dimethyl-pyridin-2-ylmethyl)-7H-pyrrolo [2,3-d]pyrimidin-5-yl]-but-3-yn-1-ol (see example 2) (4.0 g) and 1-H-tetrazole (0.45 M in acetonitrile, 70 mL) in THF (160 mL) was treated with di-tert-butyl diisopropylphosphoramidite (16.4 mL) at rt for 2 h. The solution was cooled to 0° C. and treated with 30% aqueous H2O2 (11 mL) for 30 min. Work-up (EtOAc, aq. NaHCO3) and reverse-phase preparative HPLC gave the title compound, as a solid. HPLC Rt=6.13 min.

Quellen und Nachweise

ORD-Eintrag
ord-4c744ce333734f9187fff09fd72a4ccf
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093229B2

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