Lithium iodide → HCID 86732068, Verbindung

HRID 1498806

Reaktionsgleichung

Reaktionsgleichung von HRID 1498806
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:22]=[CH:23][C:24]=1[O:25][CH3:26])[CH2:6][C:7]1[N:11]([C:12]2[CH:17]=[C:16]([CH:18]=[CH2:19])[N:15]=[C:14]([CH3:20])[N:13]=2)[N:10]=[C:9]([CH3:21])[N:8]=1.Cl[CH:28](Cl)[B:29]1[O:33][C:32]([CH3:35])([CH3:34])[C:31]([CH3:37])([CH3:36])[O:30]1.[I-].[Li+]>O1CCCC1.[Cl-].[Cr+2].[Cl-]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:22]=[CH:23][C:24]=1[O:25][CH3:26])[CH2:6][C:7]1[N:11]([C:12]2[CH:17]=[C:16]([CH:18]3[CH2:19][CH:28]3[B:29]3[O:33][C:32]([CH3:35])([CH3:34])[C:31]([CH3:37])([CH3:36])[O:30]3)[N:15]=[C:14]([CH3:20])[N:13]=2)[N:10]=[C:9]([CH3:21])[N:8]=1

Komponenten

6

Edukt 3

HCID 66321Lithium iodideHCID 110420412-(dichloromethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 71548429HCID 71548429, Verbindung

Produkt 1

HCID 86732068HCID 86732068, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 10197677chromium(II) dichlorideKatalysatorHCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

To a stirring slurry of chromium(II) chloride (630 mg, 5.12 mmol, 8.0 eq.) in dry tetrahydrofuran (10 ml) under nitrogen at 23° C. was added n,n,n′,n′-tetramethylethylenediamine (0.768 ml, 5.12 mmol, 8.0 eq.). The resulting blue reaction mixture was allowed to stir for 20 min. To the reaction mixture was added a solution of 4-(5-(3,4-dimethoxybenzyl)-3-methyl-1H-1,2,4-triazol-1-yl)-2-methyl-6-vinylpyrimidine (3-1, 225 mg, 0.640 mmol, 1.0.eq.) in tetrahydrofuran (2 mL) followed by a solution of 2-(dichloromethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (270 mg, 1.281 mmol, 2.0 eq.) and lithium iodide (343 mg, 2.56 mmol, 4.0 eq) in tetrahydrofuran (2 mL). The resulting greenish blue reaction mixture was allowed to stir for 72 h. The reaction mixture was filtered, concentrated, and partitioned between ethyl acetate (100 mL) and water (100 mL). The organic layer was separated, dried over sodium sulfate, filtered and concentrated to afford 4-(5-(3,4-dimethoxybenzyl)-3-methyl-1H-1,2,4-triazol-1-yl)-2-methyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclopropyl)pyrimidine (3-2). The crude material was carried forward with no purification. LRMS m/z (M+H) 492.5 found, 492.3 required

Aufarbeitung

  1. customThe resulting greenish blue reaction mixture
  2. stirringto stir for 72 h
  3. filtrationThe reaction mixture was filtered
  4. concentrationconcentrated
  5. custompartitioned between ethyl acetate (100 mL) and water (100 mL)
  6. customThe organic layer was separated
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-71619895d0c54f9893fb7a84fcd3cf86
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09200001B2

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