StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Triethylamine → tert-Butyl 4-(3-(4-amino-5-((benzyloxy)methyl)-2-butyl-5H-pyrrolo[3,2-d]pyrimidin-7-yl)prop-2-yn-1-yl)piperazine-1-carboxylate

HRID 1487258
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1487258
[CH2:1]([O:8][CH2:9][N:10]1[C:18]2[C:17]([NH2:19])=[N:16][C:15]([CH2:20][CH2:21][CH2:22][CH3:23])=[N:14][C:13]=2[C:12](I)=[CH:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH2:32]([N:35]1[CH2:40][CH2:39][N:38]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:37][CH2:36]1)[C:33]#[CH:34]>CN(C)C=O.CO.CS(C)=O.[Cu]I.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[NH2:19][C:17]1[C:18]2[N:10]([CH2:9][O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:11]=[C:12]([C:34]#[C:33][CH2:32][N:35]3[CH2:40][CH2:39][N:38]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:37][CH2:36]3)[C:13]=2[N:14]=[C:15]([CH2:20][CH2:21][CH2:22][CH3:23])[N:16]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 3

HCID 8471TriethylamineHCID 11287538tert-Butyl 4-(prop-2-yn-1-yl)piperazine-1-carboxylateHCID 901769325-((Benzyloxy)methyl)-2-butyl-7-iodo-5H-pyrrolo[3,2-d]pyrimidin-4-amine

Produkt 1

HCID 118453806tert-Butyl 4-(3-(4-amino-5-((benzyloxy)methyl)-2-butyl-5H-pyrrolo[3,2-d]pyrimidin-7-yl)prop-2-yn-1-yl)piperazine-1-carboxylateAusbeute 98,2 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Katalysator
HCID 6102075Dichlorobis(triphenylphosphine)palladiumKatalysator
HCID 6228DimethylformamideLösungsmittel
HCID 22036561Dimethyl sulfoxide methanolLösungsmittel

Versuchsvorschrift

To a degassed solution of 5-((benzyloxy)methyl)-2-butyl-7-iodo-5H-pyrrolo[3,2-d]pyrimidin-4-amine (150 mg, 0.344 mmol) in anhydrous N,N-dimethylformamide (3 mL) under nitrogen atmosphere at room temperature was added copper(I) iodide (13 mg, 0.068 mmol), bis(triphenylphosphine)palladium(II)dichloride (27 mg, 0.038 mmol) and, finally, triethylamine (0.086 mL, 0.619 mmol). The mixture was stirred at room temperature under nitrogen atmosphere for 10 minutes and then tert-butyl 4-(prop-2-yn-1-yl)piperazine-1-carboxylate (139 mg, 0.619 mmol) was added in one portion. The reaction mixture was heated to 55° C. in a pre-heated oil bath and stirred at 55° C. for 40 minutes. The reaction was evaporated in vacuo to yield a dark brown oil. The oil was partitioned between water and dichloromethane. The organic layer was separated and the aqueous back extracted with dichloromethane. The combined organic extracts were passed through a hydrophobic frit and evaporated in vacuo to yield a dark brown oil. The oil was dissolved in MeOH:DMSO (1:1) (2×1 mL) and purified by MDAP (Method B). Appropriate fractions were combined and evaporated in vacuo to yield the title compound as a brown oil (180 mg).

Aufarbeitung

  1. temperatureThe reaction mixture was heated to 55° C. in a pre-heated oil bath
  2. stirringstirred at 55° C. for 40 minutes
  3. customThe reaction was evaporated in vacuo
  4. customto yield a dark brown oil
  5. customThe oil was partitioned between water and dichloromethane
  6. customThe organic layer was separated
  7. extractionthe aqueous back extracted with dichloromethane
  8. customevaporated in vacuo
  9. customto yield a dark brown oil
  10. custompurified by MDAP (Method B)
  11. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e0084ef530ce4d549438b2fa77273c03
Quelldatensatz
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09428512B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion