Phosphorus oxychloride → HCID 11559938, compound

HRID 1181255Notes

Reaction equation

HRID 1181255 reaction equation
[CH:1]1([C:8]2[N:13]3[CH:14]=[CH:15][N:16]=[C:12]3[N:11]=[C:10](O)[C:9]=2[C:18]2[C:23]([F:24])=[CH:22][C:21]([F:25])=[CH:20][C:19]=2[F:26])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.P(Cl)(Cl)([Cl:29])=O>>[Cl:29][C:10]1[C:9]([C:18]2[C:19]([F:26])=[CH:20][C:21]([F:25])=[CH:22][C:23]=2[F:24])=[C:8]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]2)[N:13]2[CH:14]=[CH:15][N:16]=[C:12]2[N:11]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178517377HCID 178517377, compound

Product 1

HCID 11559938HCID 11559938, compound

Procedure

A mixture of the above 5-cycloheptyl-6-(2,4,6-trifluorophenyl)imidazo[1,2-a]pyrimidin-7-ol (294 mg) in 2 mL of phosphorous oxychloride is heated at reflux for 6 h. The excess phosphorous oxychloride is removed in vaccuo, and the resulting residue is dissolved in methylene chloride. The organic layer is washed with water, dried over magnesium sulfate, and concentrated. The residue is chromatographed over silica gel, eluting with a gradient of 10% ethyl acetate in hexanes to 33% ethyl acetate in hexanes. Concentration provides 7-chloro-5-cycloheptyl-6-(2,4,6-trifluorophenyl)imidazo[1,2-a]pyrimidine as a white solid (24 mg). MS: m/z 380.2 (M+H).

Workup

  1. temperatureis heated
  2. temperatureat reflux for 6 h
  3. customThe excess phosphorous oxychloride is removed in vaccuo
  4. dissolutionthe resulting residue is dissolved in methylene chloride
  5. washThe organic layer is washed with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue is chromatographed over silica gel
  9. washeluting with a gradient of 10% ethyl acetate in hexanes to 33% ethyl acetate in hexanes
  10. concentrationConcentration

Sources & evidence

ORD record
ord-f031efaba9e046a591d2101e45950647
Source dataset
uspto-grants-2007_10
Patent number
US07285555B2

Reaction notes

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