Hydrochloric Acid → HCID 17979104, compound

HRID 1354124Notes

Reaction equation

HRID 1354124 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[C:10]([O:12][CH2:13][C:14]([CH3:16])=[CH2:15])[N:9]=[CH:8][N:7]=1)[C:2]#[C:3][CH3:4].[ClH:17].O>C(Cl)(Cl)(Cl)Cl.[Cl-].C([N+](CCCCCCCC)(CCCCCCCC)C)CCCCCCC>[CH2:1]([O:5][C:6]1[CH:11]=[C:10]([O:12][CH2:13][C:14]([Cl:17])([CH3:16])[CH3:15])[N:9]=[CH:8][N:7]=1)[C:2]#[C:3][CH3:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 17979076HCID 17979076, compound

Product 1

HCID 17979104HCID 17979104, compound

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
0 °C

Procedure

In 1.2 ml of carbon tetrachloride were dissolved 0.15 g of 4-(2-butynyloxy)-6-(2-methylallyloxy)pyrimidine and 0.01 g of trioctylmethylammonium chloride, to which 1 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 50 minutes. 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 0.08 g of 4-(2-butynyloxy)-6-(2-chloro-2-methylpropyloxy)pyrimidine (the present compound (20)).

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-1651f8b35114426b91457d2dc44112f2
Source dataset
uspto-grants-2007_05
Patent number
US07223769B2

Reaction notes

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