Phosphorus oxychloride → HCID 86655129, compound

HRID 455156Notes

Reaction equation

HRID 455156 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][N:11]3[C:16]=2[CH2:17][C:18]2[N:23]=[CH:22][N:21]=[C:20](O)[CH:19]=2)=[CH:4][CH:3]=1.O=P(Cl)(Cl)[Cl:27]>C(#N)C.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][N:11]3[C:16]=2[CH2:17][C:18]2[CH:19]=[C:20]([Cl:27])[N:21]=[CH:22][N:23]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178515832HCID 178515832, compound

Product 1

HCID 86655129HCID 86655129, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

To a mixture of 360 mg of 6-((2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)methyl)pyrimidin-4-ol (1.07 mmol, 1 eq) in 5 mL of ACN was added 0.98 mL of POCl3 (10.7 mmol. 10 eq). The mixture was heated to 65° C. and stirred for 1 h. The solution was then diluted with EtOAc, washed with NaHCO3, dried on MgSO4, filtered and concentrated (210 mg, 55%) m/e+=355 (M+H+).

Workup

  1. washwashed with NaHCO3
  2. customdried on MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated (210 mg, 55%) m/e+=355 (M+H+)

Sources & evidence

ORD record
ord-97bf97323a8b4f27a3918dbf834ea6b3
Source dataset
uspto-grants-2013_07
Patent number
US08497278B2

Reaction notes

Loading…