Hydrochloric Acid → HCID 17979108, compound

HRID 1354142Notes

Reaction equation

HRID 1354142 reaction equation
[CH2:1]([O:6][C:7]1[CH:12]=[C:11]([O:13][CH2:14][C:15]([CH3:17])=[CH2:16])[N:10]=[CH:9][N:8]=1)[C:2]#[C:3][CH2:4][CH3:5].[ClH:18].O>C(Cl)(Cl)Cl.[Cl-].C([N+](CCCCCCCC)(CCCCCCCC)C)CCCCCCC>[CH2:1]([O:6][C:7]1[CH:12]=[C:11]([O:13][CH2:14][C:15]([Cl:18])([CH3:17])[CH3:16])[N:10]=[CH:9][N:8]=1)[C:2]#[C:3][CH2:4][CH3:5]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 17979065HCID 17979065, compound

Product 1

HCID 17979108HCID 17979108, compound

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

In 5 ml of chloroform were dissolved 0.64 g of 4-(2-pentynyloxy)-6-(2-methyl-2-propenyloxy)pyrimidine and 0.06 g of trioctylmethylammonium chloride, to which 3 ml of concentrated hydrochloric acid was added dropwise at 0° C., followed by stirring at 0° C. for 30 minutes and at room temperature for 7 hours. The reaction mixture was then poured into water, which was extracted three times with t-butyl methyl ether. The combined organic layer was washed with a saturated aqueous sodium hydrogencarbonate solution, a saturated aqueous sodium chloride solution, dried over anhydrous magnesium, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.12 g of 4-(2-pentynyloxy)-6-(2-chloro-2-methylpropyloxy)pyrimidine (the present compound (40)).

Workup

  1. extractionwas extracted three times with t-butyl methyl ether
  2. washThe combined organic layer was washed with a saturated aqueous sodium hydrogencarbonate solution
  3. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous magnesium
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7fbbd995efb04d3c913c833095dad09a
Source dataset
uspto-grants-2007_05
Patent number
US07223769B2

Reaction notes

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