Phosphorus oxychloride → Ethyl 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylate

HRID 369866

Reaction equation

HRID 369866 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:15][C:9]2[N:10]=[CH:11][N:12]=[C:13](O)[C:8]=2[CH:7]=1)=[O:5])[CH3:2].O=P(Cl)(Cl)[Cl:18]>>[Cl:18][C:13]1[C:8]2[CH:7]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[NH:15][C:9]=2[N:10]=[CH:11][N:12]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178468549HCID 178468549, compound

Product 1

HCID 21262606Ethyl 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylate

Conditions

Temperature
120 °C

Procedure

Under a N2 atmosphere, 32.0 g (154 mmol) of 6-ethoxycarbonyl-4-hydroxy-7H-pyrrolo[2,3-d]pyrimidine are suspended at RT in 308 ml (338 mmol) of POCl3 and, with stirring, heated at 120° C., during which the solid dissolves. After 3 hours' stirring at 120° C., the excess POCl3 is distilled off (65° C. external temperature; 15 mbar). The residue is suspended in 50 ml of ice-cold toluene, filtered and washed with toluene to yield the title compound; m.p. 219-221° C.; 1H-NMR (DMSO-d6) 8.77 and 7.24 (2s, 2H), 4.39 (q, J=7, 2H), 1.36 (t, J=7, 3H). Further product can be obtained from the filtrate by concentrating by evaporation and then stirring in ethyl acetate/water.

Workup

  1. dissolutiondissolves
  2. stirringAfter 3 hours' stirring at 120° C.
  3. distillationthe excess POCl3 is distilled off (65° C. external temperature; 15 mbar)
  4. filtrationfiltered
  5. washwashed with toluene

Sources & evidence

ORD record
ord-b71bace23d4840f1966be9961c9c4a79
Source dataset
uspto-grants-2000_10
Patent number
US06140332

Linked notes

Loading…