Hydrochloric Acid → HCID 17979077, compound

HRID 1354143Notes

Reaction equation

HRID 1354143 reaction equation
[CH2:1]([O:6][C:7]1[CH:12]=[C:11]([O:13][CH:14]([CH3:18])[C:15]([CH3:17])=[CH2:16])[N:10]=[CH:9][N:8]=1)[C:2]#[C:3][CH2:4][CH3:5].[ClH:19].C(=O)([O-])O.[Na+]>O1CCCC1.C(OCC)C>[CH2:1]([O:6][C:7]1[CH:12]=[C:11]([O:13][CH:14]([CH3:18])[C:15]([Cl:19])([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 516892Sodium BicarbonateHCID 17979078HCID 17979078, compound

Product 1

HCID 17979077HCID 17979077, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution containing 0.3 g of 4-(2-pentynyloxy)-6-(1,2-dimethyl-2-propenyloxy)pyrimidine in 3 ml of tetrahydrofuran was added dropwise 3.66 ml of a 1 mol/l solution of hydrogen chloride in diethyl ether, followed by stirring at room temperature for 9 hours. The reaction mixture was then poured into a saturated aqueous sodium hydrogencarbonate solution, which was extracted three times with t-butyl methyl ether. The combined organic layers were washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium chloride, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.07 g of 4-(2-pentynyloxy)-6-(2-chloro-1,2-dimethylpropyloxy)pyrimidine (the present compound (41)).

Workup

  1. extractionwas extracted three times with t-butyl methyl ether
  2. washThe combined organic layers were washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium chloride
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c08280df859447388ef0f48d068498ef
Source dataset
uspto-grants-2007_05
Patent number
US07223769B2

Reaction notes

Loading…