Phosphorus oxychloride → 4-Chloro-2-pyridin-2-yl-7H-pyrrolo[2,3-d]pyrimidine

HRID 1878609Notes

Reaction equation

HRID 1878609 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:8]=[C:9](O)[C:10]2[CH:15]=[CH:14][NH:13][C:11]=2[N:12]=1.O=P(Cl)(Cl)[Cl:19]>>[Cl:19][C:9]1[C:10]2[CH:15]=[CH:14][NH:13][C:11]=2[N:12]=[C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[N:8]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178517492HCID 178517492, compound

Product 1

HCID 866324274-Chloro-2-pyridin-2-yl-7H-pyrrolo[2,3-d]pyrimidine

Conditions

Temperature
110 °C

Procedure

2-Pyridin-2-yl-7H-pyrrolo[2,3-d]pyrimidin-4-ol (1 eq, 5.56 mmol, 1.18 g) is added to POCl3 (10 ml), and the resulting mixture is heated at 110° C. for 18 h. The mixture is concentrated in vacuo and then water is added. The aqueous solution is heated at 40° C. for 15 min, cooled down to r.t., and adjusted to pH 9 with aqueous NaOH solution (8 M). The resulting precipitate is filtered and washed with water and MeOH to give the title compound; [M+H]+=231.

Workup

  1. concentrationThe mixture is concentrated in vacuo
  2. additionwater is added
  3. temperatureThe aqueous solution is heated at 40° C. for 15 min
  4. temperaturecooled down to r.t.
  5. filtrationThe resulting precipitate is filtered
  6. washwashed with water and MeOH

Sources & evidence

ORD record
ord-7cf8839866fc4a5c84dd80be5cfac8a8
Source dataset
uspto-grants-2012_11
Patent number
US08314112B2

Reaction notes

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