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Potassium Carbonate → tert-butyl 4-(7-bromo-5-methyl-5H-pyrrolo[3,2-d]pyrimidin-4-yloxy)piperidine-1-carboxylate

HRID 532481
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 532481
[Br:1][C:2]1[C:6]2[N:7]=[CH:8][N:9]=[C:10](Cl)[C:5]=2[N:4]([CH3:12])[CH:3]=1.[OH:13][CH:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1.C([O-])([O-])=O.[K+].[K+]>CN(C)C=O>[Br:1][C:2]1[C:6]2[N:7]=[CH:8][N:9]=[C:10]([O:13][CH:14]3[CH2:15][CH2:16][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:18][CH2:19]3)[C:5]=2[N:4]([CH3:12])[CH:3]=1
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Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 722079627-bromo-4-chloro-5-methyl-5H-pyrrolo[3,2-d]pyrimidine

Produkt 1

HCID 68299293tert-butyl 4-(7-bromo-5-methyl-5H-pyrrolo[3,2-d]pyrimidin-4-yloxy)piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228Dimethylformamide
Lösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To 7-bromo-4-chloro-5-methyl-5H-pyrrolo[3,2-d]pyrimidine (200 mg) obtained in Step 4-4 of Preparation Example 4, t-butyl 4-hydroxypiperidine-1-carboxylate (180 mg), K2CO3 (168 mg) and N,N-dimethylformamide (4 ml) were added, and stirred at 100° C. for 12 hours in a hermetically sealed reactor. The reaction mixture was cooled to room temperature, extracted with ethyl acetate and distilled water, and the organic layer thus obtained was washed with water and a saline solution. Subsequently, the washed organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain the title compound.

Aufarbeitung

  1. additionwere added
  2. temperatureThe reaction mixture was cooled to room temperature
  3. extractionextracted with ethyl acetate
  4. distillationdistilled water
  5. customthe organic layer thus obtained
  6. washwas washed with water
  7. dry with materialSubsequently, the washed organic layer was dried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-1842d083bfee42a190eadb7ea630c9e3
Quelldatensatz
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08853213B2

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