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

HRID 853285Notes

Reaction equation

HRID 853285 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 mixture was cooled to room temperature and the reaction mixture was concentrated. 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 brine, 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. temperaturethe reaction mixture was cooled to room temperature
  3. concentrationthe reaction mixture was concentrated
  4. additionIce water was added to the residue, and liquid separation and extraction
  5. additionmixed solvent
  6. washThe organic layer was washed with water and saturated brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-54b1bacb06104ec8a76ec61d52f62ad7
Source dataset
uspto-grants-2007_08
Patent number
US07253286B2

Reaction notes

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