Tetrahydrofuran → HCID 68327457, compound

HRID 1754230Notes

Reaction equation

HRID 1754230 reaction equation
[Li+].[Cl-].CO[C:5]1[CH:12]=[CH:11][C:8]([CH2:9]Cl)=[CH:7][CH:6]=1.Br[C:14]1[CH:15]=[N:16][CH:17]=[N:18][CH:19]=1.C1C[O:23][CH2:22]C1>[Zn].Cl[Ni](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.II.BrC(Br)C>[CH3:22][O:23][CH:9]([C:15]1[CH:14]=[CH:19][N:18]=[CH:17][N:16]=1)[C:8]1[CH:7]=[CH:6][CH:5]=[CH:12][CH:11]=1

Participants

9

Reactant 4

HCID 8028TetrahydrofuranHCID 699934-Methyloxybenzyl chlorideHCID 783445-BromopyrimidineHCID 433294Lithium Chloride

Product 1

HCID 68327457HCID 68327457, compoundYield 94%

Reagents, catalysts & solvents 4

HCID 807IodineCatalystHCID 112011,1-DibromoethaneCatalystHCID 23994ZincCatalystHCID 178418751HCID 178418751, compoundCatalyst

Procedure

A suspension of zinc dust (1300 mg, 20 mmol), LiCl (420 mg, 10 mmol), I2 (10 mg), dibromoethane (50 mg) in THF (20 mL) was heated to reflux for 15 min. and then treated with 4-methoxybenzyl chloride (16) (1.56 g, 10 mmol). Heating was continued for 6 h and the suspension was then cooled to rt before being treated (Ph3P)2NiCl2 (50 mg). The resulting red suspension was treated with 4 (1.56 g, 10 mmol) and the mixture was stirred for an extra 10 min. before being washed with NH4Cl and saturated NaHCO3. The organic layer was evaporated under reduced pressure to afford a pale yellow oil (3.03 g, 94%), which was found to be pure 17 by NMR. 1H NMR (300 MHz, CDCl3) δ ppm 9.01 (s, 1H), 8.55 (s, 2H), 7.95 (d, 2H), 7.39 (d, 2H), 4.12 (s, 2H), 3.52 (s, 3H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 15 min.
  3. temperatureHeating
  4. washbefore being washed with NH4Cl and saturated NaHCO3
  5. customThe organic layer was evaporated under reduced pressure

Sources & evidence

ORD record
ord-1464819d7b8c49a8b6c38f394d666c86
Source dataset
uspto-grants-2015_10
Patent number
US09169216B2

Reaction notes

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