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Hydrochloric Acid → N-phenyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine

HRID 930497
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 930497
[NH:1]([C:8]1[N:9]=[CH:10][C:11]2[CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14][C:12]=2[N:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>CC(C)=O.CC(O)C>[C:2]1([NH:1][C:8]2[N:9]=[CH:10][C:11]3[CH2:17][NH:16][CH2:15][CH2:14][C:12]=3[N:13]=2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 45106267t-butyl 2-anilino-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate

Produkt 1

HCID 104609480N-phenyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

A solution of t-butyl 2-anilino-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate, Intermediate 7 (2.51 g, 7.69 mmol) in acetone (20 mL) was treated with 5-6 N HCl solution in i-PrOH (6 mL) and the reaction mixture was stirred at room temperature for 27 hours. The solvent was removed in vacuo and the salt was dissolved in water. The aqueous layer was washed with EtOAc and basified with 1.0 N NaOH(aq). The alkaline mixture was extracted with CH2Cl2 (2×100 mL) and the combined CH2Cl2 extracts were dried (MgSO4), filtered, and concentrated to a yellow, crystalline solid (1.25 g, 72%).

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. dissolutionthe salt was dissolved in water
  3. washThe aqueous layer was washed with EtOAc
  4. extractionThe alkaline mixture was extracted with CH2Cl2 (2×100 mL)
  5. dry with materialthe combined CH2Cl2 extracts were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated to a yellow, crystalline solid (1.25 g, 72%)

Quellen und Nachweise

ORD-Eintrag
ord-5575d9c12b7741a5b3d6eff9fb0ce7ee
Quelldatensatz
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09296747B1

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