Phosphorus oxychloride → HCID 86610853, compound

HRID 2105227Notes

Reaction equation

HRID 2105227 reaction equation
[CH:1]1([C:4]2[CH:8]=[C:7]([CH:9]3[CH2:13][CH2:12][CH2:11][N:10]3[C:14]3[N:19]=[C:18](O)[CH:17]=[C:16]([CH2:21][O:22][CH3:23])[N:15]=3)[O:6][N:5]=2)[CH2:3][CH2:2]1.P(Cl)(Cl)([Cl:26])=O>>[Cl:26][C:18]1[CH:17]=[C:16]([CH2:21][O:22][CH3:23])[N:15]=[C:14]([N:10]2[CH2:11][CH2:12][CH2:13][CH:9]2[C:7]2[O:6][N:5]=[C:4]([CH:1]3[CH2:3][CH2:2]3)[CH:8]=2)[N:19]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178494554HCID 178494554, compound

Product 1

HCID 86610853HCID 86610853, compoundYield 85.7%

Procedure

A mixture of 2-[2-(3-cyclopropylisoxazol-5-yl]pyrrolidin-1-yl]-4-hydroxy-6-methoxymethylpyrimidine (Method 18) (563 mg, 1.78 mmol) and phosphoryl chloride (1 ml, 10.7 mmol) was heated at reflux for 45 minutes. The volatiles were removed by evaporation, the residue dissolved in DCM, washed with saturated aqueous sodium hydrogen carbonate solution, dried (Na2SO4) and evaporated. The residue was purified by chromatography on silica gel eluting with DCM/diethyl ether (100:0 and then 80:20) to give the title compound (511 mg, 81%) as a yellow oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 45 minutes
  3. customThe volatiles were removed by evaporation
  4. dissolutionthe residue dissolved in DCM
  5. washwashed with saturated aqueous sodium hydrogen carbonate solution
  6. dry with materialdried (Na2SO4)
  7. customevaporated
  8. customThe residue was purified by chromatography on silica gel eluting with DCM/diethyl ether (100:0

Sources & evidence

ORD record
ord-962929f813a349a2bd1d3e75eeaf79fa
Source dataset
uspto-grants-2009_08
Patent number
US07579349B2

Reaction notes

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