Water → HCID 17979121, compound

HRID 1354131Notes

Reaction equation

HRID 1354131 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[C:10]([O:12][CH2:13][C:14](O)([CH3:16])[CH3:15])[N:9]=[CH:8][N:7]=1)[C:2]#[C:3][CH3:4].CCN(S(F)(F)[F:24])CC.O>C(Cl)(Cl)Cl>[CH2:1]([O:5][C:6]1[CH:11]=[C:10]([O:12][CH2:13][C:14]([F:24])([CH3:16])[CH3:15])[N:9]=[CH:8][N:7]=1)[C:2]#[C:3][CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 123472(Diethylamino)sulfur trifluorideHCID 17979111HCID 17979111, compound

Product 1

HCID 17979121HCID 17979121, compoundYield 63.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

First, 0.33 g of 4-(2-butynyloxy)-6-(2-hydroxy-2-methylpropyloxy)pyrimidine was dissolved in 3 ml of chloroform, to which 0.5 ml of a solution containing 0.25 g of DAST in chloroform was added dropwise at 0° C., followed by stirring for 30 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 0.21 g of 4-(2-butynyloxy)-6-(2-fluoro-2-methylpropyloxy)pyrimidine (the present compound (28)).

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-2fcc13ecec1141158c303ec2226bb5bd
Source dataset
uspto-grants-2007_05
Patent number
US07223769B2

Reaction notes

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