Water → HCID 17979122, compound

HRID 1354121Notes

Reaction equation

HRID 1354121 reaction equation
[CH2:1]([O:6][C:7]1[CH:12]=[C:11]([O:13][CH:14]([CH3:19])[C:15](O)([CH3:17])[CH3:16])[N:10]=[CH:9][N:8]=1)[C:2]#[C:3][CH2:4][CH3:5].CCN(S(F)(F)[F:26])CC.O>C(Cl)(Cl)Cl>[F:26][C:15]([CH3:17])([CH3:16])[CH:14]([CH3:19])[O:13][C:11]1[CH:12]=[C:7]([O:6][CH2:1][C:2]#[C:3][CH2:4][CH3:5])[N:8]=[CH:9][N:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 123472(Diethylamino)sulfur trifluorideHCID 17979099HCID 17979099, compound

Product 1

HCID 17979122HCID 17979122, compoundYield 51.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

First, 0.31 g of 4-(2-pentynyloxy)-6-(2-hydroxy-1,2-dimethylpropyloxy)pyrimidine was dissolved in 3 ml of chloroform, to which 0.5 ml of a solution containing 0.24 g of DAST in chloroform was added dropwise at 0° C., followed by stirring for 10 minutes. The reaction mixture was then poured into water, which was extracted three times with chloroform. The combined organic layers were washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.16 g of 4-(2-fluoro-1,2-dimethylpropyloxy)-6-(2-pentynyloxy)pyrimidine (the present compound (17)).

Workup

  1. additionwas added dropwise at 0° C.
  2. extractionwas extracted three times with chloroform
  3. washThe combined organic layers were washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-25b64a85f8804277a1238c9b251c78b9
Source dataset
uspto-grants-2007_05
Patent number
US07223769B2

Reaction notes

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