Ammonium Chloride → HCID 22599888, compound

HRID 1592204Notes

Reaction equation

HRID 1592204 reaction equation
C(N(C(C)C)CC)(C)C.[CH2:10]([O:14][C:15]1[CH:20]=[C:19](Cl)[N:18]=[CH:17][N:16]=1)[C:11]#[C:12][CH3:13].[F:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[SH:29].[Cl-].[NH4+]>C(Cl)(Cl)Cl>[CH2:10]([O:14][C:15]1[CH:20]=[C:19]([S:29][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[F:22])[N:18]=[CH:17][N:16]=1)[C:11]#[C:12][CH3:13]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 5202162-FluorothiophenolHCID 121376024-(2-Butynyloxy)-6-chloropyrimidine

Product 1

HCID 22599888HCID 22599888, compoundYield 23.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 2.2 ml of chloroform were added 0.29 ml of diisopropylethylamine, 0.2 g of 4-(2-butynyloxy)-6-chloropyrimidine, and 0.17 g of 2-fluorothiophenol, followed by stirring at room temperature for 7 hours. Then, a saturated aqueous ammonium chloride solution was poured into the reaction mixture, which was extracted three times with t-butyl methyl ether. The organic layers were combined, washed with water, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.07 g of 4-(2-butynyloxy)-6-(2-fluorophenylthio)pyrimidine (the present compound (146)).

Workup

  1. extractionwas extracted three times with t-butyl methyl ether
  2. washwashed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b53c3e337e474104a460cd6066c37654
Source dataset
uspto-grants-2007_11
Patent number
US07291730B2

Reaction notes

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