Ammonium Chloride → HCID 53921277, compound

HRID 1592203Notes

Reaction equation

HRID 1592203 reaction equation
CC(C)([O-])C.[K+].FC1C=CC=CC=1CC#N.Cl[C:18]1[CH:23]=[C:22]([O:24][CH2:25][C:26]#[C:27][CH3:28])[N:21]=[CH:20][N:19]=1.[Cl-].[NH4+]>O1CCCC1>[CH2:25]([O:24][C:22]1[N:21]=[CH:20][N:19]=[CH:18][CH:23]=1)[C:26]#[C:27][CH3:28]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 67592Benzeneacetonitrile, 2-fluoro-HCID 121376024-(2-Butynyloxy)-6-chloropyrimidineHCID 23665647Potassium tert-butoxide

Product 1

HCID 53921277HCID 53921277, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In 40 ml of tetrahydrofuran was suspended 4.61 g of potassium t-butoxide, to which 4.44 g of (2-fluorophenyl)acetonitrile was added under ice cooling. Then, a solution of 5.00 g of 4-chloro-6-(2-butynyloxy)pyrimidine in 20 ml of tetrahydrofuran was added at 0° C., followed by stirring at room temperature for 4 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution and extracted three times with chloroform. The chloroform layers were combined and washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then concentrated. The residue was subjected to silica gel column chromatography to give 6.40 g of 4-α-cyano-2-fluorobenzyl)-6-(2-butynyloxy)pyrimidine (the present compound (145)).

Workup

  1. extractionextracted three times with chloroform
  2. washwashed with a saturated aqueous sodium chloride solution
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4c2f361cfbda4b79b0e3c88ddd3d9f6a
Source dataset
uspto-grants-2007_11
Patent number
US07291730B2

Reaction notes

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