Phosphorus oxychloride → HCID 86632628, compound

HRID 1695558Notes

Reaction equation

HRID 1695558 reaction equation
C(OC(=O)[NH:7][CH:8]([C:16]1[CH:21]=[C:20]([Cl:22])[N:19]=[CH:18][N:17]=1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(C)(C)C.P(Cl)(Cl)(Cl)=O>C(Cl)Cl>[Cl:22][C:20]1[N:19]=[CH:18][N:17]=[C:16]([CH:8]([NH2:7])[CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:21]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 86632629HCID 86632629, compound

Product 1

HCID 86632628HCID 86632628, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

[1-(6-Chloro-pyrimidin-4-yl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester: A white suspension of 10A (1.39 g, 4.41 mmol) in phosphorus oxychloride (20.54 mL, 220 mmol) was warmed to 50° C. to give a clear, pale yellow solution. After 3 h, the orange-brown solution was cooled to rt and concentrated in vacuo to give an orange-brown residue. The residue was dissolved in CH2Cl2 and concentrated (2×). The residue was dissolved in CH2Cl2 and sat. NaHCO3 was added. The mixture was stirred vigorously for 10-15 min. The layers were separated and the aqueous layer was extracted with CH2Cl2 (1×). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated to give 0.990 g of 1-(6-chloropyrimidin-4-yl)-2-phenylethanamine as a thick, viscous orange-brown residue. MS 234.0 (M+H)+; 236 (M+2+H)+.

Workup

  1. customto give a clear, pale yellow solution
  2. temperaturethe orange-brown solution was cooled to rt
  3. concentrationconcentrated in vacuo
  4. customto give an orange-brown residue
  5. concentrationconcentrated (2×)
  6. dissolutionThe residue was dissolved in CH2Cl2
  7. additionsat. NaHCO3 was added
  8. customThe layers were separated
  9. extractionthe aqueous layer was extracted with CH2Cl2 (1×)
  10. washThe combined organic layers were washed with brine
  11. dry with materialdried over MgSO4
  12. filtrationfiltered
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-ff940673bec44bb59fdc9bab03db39b3
Source dataset
uspto-grants-2012_04
Patent number
US08163749B2

Reaction notes

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