Hydrochloric Acid → 2-chloro-9-methyl-6-((R)-3-methylmorpholin-4-yl)-9H-purine-8-carbaldehyde

HRID 1945692Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1945692
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH3:11])=[C:4]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][C@H:13]2[CH3:18])[N:3]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.CN([CH:32]=[O:33])C.Cl>C1COCC1>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([CH:32]=[O:33])[N:8]2[CH3:11])=[C:4]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][C@H:13]2[CH3:18])[N:3]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 2733832Lithium HexamethyldisilazideHCID 59605958HCID 59605958, Verbindung

Produkt 1

HCID 596059322-chloro-9-methyl-6-((R)-3-methylmorpholin-4-yl)-9H-purine-8-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 2-chloro-9-methyl-6-((R)-3-methylmorpholin-4-yl)-9H-purine (550 mg, 2.05 mmol) in THF (20 mL) at −78° C. was added LiHMDS (3.1 mL, 3.08 mmol, 1M solution in THF). The resulting mixture was allowed to stir for 45 min before the addition of DMF (800 μL, 10.33 mmol). The reaction mixture was warmed to r.t. over 1.5 h then poured onto 0.5M HCl. The resulting precipitate was collected by filtration and washed with H2O then Et2O affording the title compound as a yellow solid (406 mg, 67%). LCMS (method H): RT 3.35 min [M+H]+ 296.3

Aufarbeitung

  1. filtrationThe resulting precipitate was collected by filtration
  2. washwashed with H2O
  3. customRT 3.35 min [M+H]+ 296.3

Quellen und Nachweise

ORD-Eintrag
ord-1953801b50a449cf96cb50adc3bb85f2
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08394796B2

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