Hydrochloric Acid → 4-(2-Butynyloxy)-6-(2-chloro-1,2-dimethylpropyloxy)pyrimidine

HRID 1354136Notes

Reaction equation

[CH2:1]([O:5][C:6]1[CH:11]=[C:10]([O:12][CH:13]([CH3:17])[C:14]([CH3:16])=[CH2:15])[N:9]=[CH:8][N:7]=1)[C:2]#[C:3][CH3:4].[ClH:18].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][CH:13]([CH3:17])[C:14]([Cl:18])([CH3:16])[CH3:15])[N:9]=[CH:8][N:7]=1)[C:2]#[C:3][CH3:4]

Participants

Conditions

Temperature: 0 °C

Procedure

In 3 ml of carbon tetrachloride were dissolved 0.23 g of 4-(2-butynyloxy)-6-(1,2-dimethylallyloxy)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 3 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 0.05 g of 4-(2-butynyloxy)-6-(2-chloro-1,2-dimethylpropyloxy)pyrimidine (the present compound (34)).

Workup

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

Sources & evidence

ORD record: ord-8377b07e8e8e4e728e2f9e98cce007d5
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07223769B2

Reaction notes

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