Triethylamine → Carbonic Acid 4-(dimethylamino-methyleneamino)-5-fluoropyrimidin-2-yl Ester Ethyl Ester

HRID 705578Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 705578
[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(N(CC)CC)C.Cl[C:22]([O:24][CH2:25][CH3:26])=[O:23]>C(Cl)Cl>[CH2:25]([O:24][C:22](=[O:23])[O:8][C:5]1[N:4]=[C:3]([N:9]=[CH:10][N:11]([CH3:13])[CH3:12])[C:2]([F:1])=[CH:7][N:6]=1)[CH3:26]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 178484257HCID 178484257, Verbindung

Produkt 1

HCID 57818850Carbonic Acid 4-(dimethylamino-methyleneamino)-5-fluoropyrimidin-2-yl Ester Ethyl EsterAusbeute 22,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of N′-(5-fluoro-2-hydroxy-pyrimidin-4-yl)-N,N-dimethylformamidine (0.10, 0.54 mmol) in CH2Cl2 (2 mL) were added triethylamine (0.20 g, 2.0 mmol) and ethyl chloroformate (0.065 g, 0.60 mmol), and the mixture was agitated on an orbital shaker at room temperature overnight. The reaction was diluted with CH2Cl2 and the solution was washed with water, dried over MgSO4, filtered and evaporated. The crude product was purified by silica gel column chromatography (EtOAc/petroleum ether gradient) to yield 0.031 g (22%) of the title compound as a white solid: mp 124-126° C.; 1H NMR (300 MHz, CDCl3) δ 8.67 (s, 1H), 8.19 (d, J=2.2 Hz, 1H), 4.35 (q, J=7.14 Hz, 2H), 3.21 (s, 6H), 1.40 (t, J=7.14 Hz, 3H); HPLC-MS (ESI) m/z 258 (M+H)+.

Aufarbeitung

  1. washthe solution was washed with water
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude product was purified by silica gel column chromatography (EtOAc/petroleum ether gradient)

Quellen und Nachweise

ORD-Eintrag
ord-78912ea571e343edbb101a4b84c8528b
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09174970B2

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