1-Pentyne → 2-(4'-Fluorophenyl)-5-pent-1-ynylpyrimidine

HRID 1603308

Reaktionsgleichung

Reaktionsgleichung von HRID 1603308
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[CH:12][C:11](Br)=[CH:10][N:9]=2)=[CH:4][CH:3]=1.[CH:15]#[C:16][CH2:17][CH2:18][CH3:19].FC1C(F)=C(OCCCCCCCC)C=CC=1C1N=CC(C#CCCCCCCC)=CN=1>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.[Cu]I.C(NC(C)C)(C)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[CH:12][C:11]([C:15]#[C:16][CH2:17][CH2:18][CH3:19])=[CH:10][N:9]=2)=[CH:4][CH:3]=1

Komponenten

7

Edukt 3

HCID 123091-PentyneHCID 232970645-Bromo-2-(4-fluorophenyl)pyrimidineHCID 544551022-(2',3'-Difluoro-4'-octyloxyphenyl)-5-non-1-ynylpyrimidine

Produkt 1

HCID 193862632-(4'-Fluorophenyl)-5-pent-1-ynylpyrimidineAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418397HCID 178418397, VerbindungKatalysatorHCID 7912DiisopropylamineLösungsmittel

Versuchsvorschrift

--Quantities: 2-(4'-fluorophenyl)-5-bromo-pyrimidine 20 (1.48 g, 4.88 mmol), pent-1-yne (0.98 ml, 10 mmol), tetrakis(triphenylphosphine)palladium (350 mg, 0.30 mmol), copper(I) iodide (57 mg, 0.30 mmol), diisopropylamine (20 ml). The experimental procedure was as described for compound 38. The crude product was purified by flash chromatography (8% ethyl acetate-light petroleum) to give the fluorophenylpyrimidine 42 (1.02 g, 85%), m.p. 51° C.; νmax /cm-1 (KBr) 2960, 2870, 2220, 1600, 1510, 1430, 1220, 1150 and 855; δ 1.07 (3H, t, Me), 1.68 (2H, sext, CH2CH3), 2.47 (2H, t, CH2C≡C), 7.18 (2H, t, 3'- and 5'-H), 8.44 (2H, dd, 2'- and 6'-H) and 8.75 (2H, s, 4- and 6-H); m/z 240 (M+), 225, 212, 198, 184, 171 and 118.

Aufarbeitung

  1. customThe crude product was purified by flash chromatography (8% ethyl acetate-light petroleum)

Quellen und Nachweise

ORD-Eintrag
ord-ed1bb7e6f9554ff6afd79009163be1ae
Quelldatensatz
uspto-grants-1999_11
Patentnummer
US05986096

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