Benzoyl chloride → Benzoic Acid 4-(dimethylamino-methyleneamino)-5-fluoropyrimidin-2-yl Ester

HRID 705579Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 705579
[F:1][C:2]1[C:3]([N:9]=[CH:10][N:11]([CH3:13])[CH3:12])=[N:4][C:5]([OH:8])=[N:6][CH:7]=1.[C:14](Cl)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>N1C=CC=CC=1>[CH3:12][N:11]([CH:10]=[N:9][C:3]1[C:2]([F:1])=[CH:7][N:6]=[C:5]([O:8][C:14](=[O:21])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:4]=1)[CH3:13]

Komponenten

4

Edukt 2

HCID 7412Benzoyl chlorideHCID 178484257HCID 178484257, Verbindung

Produkt 1

HCID 57818967Benzoic Acid 4-(dimethylamino-methyleneamino)-5-fluoropyrimidin-2-yl EsterAusbeute 94,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a suspension of N′-(5-fluoro-2-hydroxypyrimidin-4-yl)-N,N-dimethylformamidine (0.10 g, 0.54 mmol) in pyridine (2 mL) was added benzoyl chloride (0.084 g, 0.60 mmol), and the mixture was agitated on an orbital shaker for 16 h at RT. The reaction mixture was partitioned between EtOAc and saturated aq NaHCO3, and the organic phase was dried over solid MgSO4, filtered, and evaporated to give the title compound (0.147 g 94%) as a white solid: mp 136-138° C.; 1H NMR (300 MHz, CDCl3) δ 8.69 (s, 1H), 8.27 (d, J=2.4 Hz, 2H), 8.25-8.20 (m, 2H), 7.69-7.63 (m, 1H), 7.56-7.49 (m, 2H), 3.23 (s, 3H), 3.20 (s, 3H); HPLC-MS (ESI) m/z 289 (M+H)+.

Aufarbeitung

  1. customThe reaction mixture was partitioned between EtOAc and saturated aq NaHCO3
  2. dry with materialthe organic phase was dried over solid MgSO4
  3. filtrationfiltered
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-bb488616f0434be7846fc97f08924851
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09174970B2

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