Phosphorus oxychloride → 6-(4-Benzyloxyphenyl)-4-chloro-7H-pyrrolo[2,3-d]pyrimidine

HRID 387762Notes

Reaction equation

HRID 387762 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[NH:24][C:18]3[N:19]=[CH:20][N:21]=[C:22](O)[C:17]=3[CH:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:27])=O>>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[NH:24][C:18]3[N:19]=[CH:20][N:21]=[C:22]([Cl:27])[C:17]=3[CH:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178518056HCID 178518056, compound

Product 1

HCID 589314296-(4-Benzyloxyphenyl)-4-chloro-7H-pyrrolo[2,3-d]pyrimidine

Conditions

Temperature
140 °C

Procedure

After adding 200 ml of phosphorus oxychloride to 20 g of the 6-(4-benzyloxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ol synthesized in Production Example 153-2, the mixture was stirred at 140° C. for 3 hours and the reaction system was concentrated at room temperature. Ice water was added to the residue, and liquid separation and extraction were performed with an ethyl acetate:tetrahydrofuran (5:1) mixed solvent. The organic layer was washed with water and saturated saline, dried over sodium sulfate and concentrated to dryness to obtain 12 g of the title compound.

Workup

  1. customsynthesized in Production Example 153-2
  2. concentrationthe reaction system was concentrated at room temperature
  3. additionIce water was added to the residue, and liquid separation and extraction
  4. additionmixed solvent
  5. washThe organic layer was washed with water and saturated saline
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-a23738d5d3154c659ee20f3059a7e56f
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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