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Potassium Carbonate → 6-Benzyl-4-(2-chloro-phenyl)-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-2-ylamine

HRID 1020008
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1020008
[CH2:1]([N:8]1[CH2:19][CH2:18][C:11]2[N:12]=[C:13]([NH2:17])[N:14]=[C:15](Cl)[C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1B(O)O.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([N:8]1[CH2:19][CH2:18][C:11]2[N:12]=[C:13]([NH2:17])[N:14]=[C:15]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[Cl:20])[C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
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Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 27343222-Chlorophenylboronic acidHCID 143932216-Benzyl-4-chloro-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine

Produkt 1

HCID 497874276-Benzyl-4-(2-chloro-phenyl)-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-2-ylamineAusbeute 61,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 962WaterLösungsmittel
HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

6-benzyl-4-chloro-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-2-ylamine (1.92 g., 7 mmoles) and 2-chlorophenylboronic acid (1.09 g., 7 mmoles) were mixed and stirred in a mixture of acetonitrile and water (50:50, 32 mls); anhydrous potassium carbonate (1.93 g., 14 mmoles) was then added to the stirred reaction mixture under nitrogen. Pd(PPh3)4 (0.2 g.) was then added to the reaction mixture which was stirred and heated at 95° C. for 3 hours also under nitrogen. The reaction mixture was then allowed to cool to room temperature and a beige solid formed. This suspension was quenched with water (150 mls) and the solid filtered and washed with water (100 mls) dried in a vacuum desiccator. The product was then eluted through a ‘silica plug’ in ethyl acetate, after evaporation the solid was slurried in ether to give, after filtering and drying a white solid (1.5 g., 61.2% yield). LC-MS (retention 2.65 mins, mass 351 M+H).

Aufarbeitung

  1. temperatureto cool to room temperature
  2. customa beige solid formed
  3. customThis suspension was quenched with water (150 mls)
  4. filtrationthe solid filtered
  5. washwashed with water (100 mls)
  6. customdried in a vacuum desiccator
  7. washThe product was then eluted through a ‘silica plug’ in ethyl acetate
  8. customafter evaporation the solid
  9. customto give
  10. filtrationafter filtering
  11. customdrying a white solid (1.5 g., 61.2% yield)
  12. customLC-MS (retention 2.65 mins, mass 351 M+H)

Quellen und Nachweise

ORD-Eintrag
ord-a4842633536f48f795580456c4b2ddd4
Quelldatensatz
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08716302B2

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