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Lithium Chloride → 2-benzyl-5-(4-(benzyloxy)-3-fluorophenyl)pyrimidin-4(3H)-one

HRID 1676297
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Reaktionsgleichung

Reaktionsgleichung von HRID 1676297
[CH2:1]([C:8]1[NH:13][C:12](=[O:14])[C:11](Br)=[CH:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:16]([O:23][C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][C:25]=1[F:33])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[Cl-].[Li+]>O1CCOCC1.C([O-])([O-])=O.[Na+].[Na+].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]([C:8]1[NH:13][C:12](=[O:14])[C:11]([C:27]2[CH:28]=[CH:29][C:24]([O:23][CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[C:25]([F:33])[CH:26]=2)=[CH:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 433294Lithium ChlorideHCID 27377884-Benzyloxy-3-fluorophenylboronic AcidHCID 663163592-benzyl-5-bromopyrimidin-4(3H)-one

Produkt 1

HCID 673487352-benzyl-5-(4-(benzyloxy)-3-fluorophenyl)pyrimidin-4(3H)-oneAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 10340Sodium CarbonateLösungsmittel
HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of 2-benzyl-5-bromopyrimidin-4(3H)-one (0.300 g, 1.13 mmol), 4-(benzyloxy)-3-fluorophenylboronic acid (0.334 g, 1.36 mmol), Pd(PPh3)4 (0.065 g, 0.057 mmol) and lithium chloride (0.240 g, 5.66 mmol) in dioxane (3 mL) and 2 M aq Na2CO3 (0.3 mL) was stirred at 100° C. for 18 hours. The reaction mixture was partitioned between EtOAc and H2O. The phases were separated, and the aqueous phase was re-extracted with EtOAc (3×). The combined organic layers were dried (Na2SO4), filtered and concentrated to yield a crude dark yellow solid. Purification of the crude product was achieved by trituration with dichloromethane. The resulting solid was filtered, washed with dichloromethane, collected and dried under vacuum. The filtrate was concentrated and the trituration procedure was repeated (2×) with EtOAc. The solids were combined to yield the desired product (0.284 g, 65%) as a pale yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 12.93 (br s, 1H), 8.13 (s, 1H), 7.66 (dd, J=2.3, 13.3 Hz, 1H), 7.53-7.22 (s, 12H), 5.21 (s, 2H), 3.90 (s, 2H). LRMS (APCI pos) m/e 387 (M+1).

Aufarbeitung

  1. customThe reaction mixture was partitioned between EtOAc and H2O
  2. customThe phases were separated
  3. extractionthe aqueous phase was re-extracted with EtOAc (3×)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto yield a crude dark yellow solid
  8. customPurification of the crude product
  9. filtrationThe resulting solid was filtered
  10. washwashed with dichloromethane
  11. customcollected
  12. customdried under vacuum
  13. concentrationThe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-e85b49cc1c8c4f639619ddbcb5c9be21
Quelldatensatz
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08003662B2

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