Phosphorus oxychloride → 7-Benzyl-4-chloro-2-methyl-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine

HRID 984893Notes

Reaction equation

HRID 984893 reaction equation
[CH2:1]([N:8]1[CH2:17][CH2:16][C:15]2[C:14](=O)[NH:13][C:12]([CH3:19])=[N:11][C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:22])=O>>[CH2:1]([N:8]1[CH2:17][CH2:16][C:15]2[C:14]([Cl:22])=[N:13][C:12]([CH3:19])=[N:11][C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 135553026HCID 135553026, compound

Product 1

HCID 223286927-Benzyl-4-chloro-2-methyl-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine

Procedure

7-Benzyl-2-methyl-5,6,7,8-tetrahydro-3H-pyrido[3,4-d]pyrimidin-4-one (prepared according to the method of Example 86, Step A, 17.1 g, 67.0 mmol) was suspended in phosphorus oxychloride (66 mL, 335 mmol). This mixture was stirred at reflux for 1 h, cooled to room temperature, evaporated, then chased with toluene. The residue was carefully diluted with ice/water/chloroform and the layers were separated. The aqueous phase was extracted with chloroform (3×) and the combined organic extracts were washed with saturated aqueous sodium bicarbonate (1×) and water (1×), dried over sodium sulfate, filtered, and evaporated to give the title compound of Example 86, Step B as a brown oil that was used without purification in the next step.

Workup

  1. temperatureat reflux for 1 h
  2. customevaporated
  3. additionThe residue was carefully diluted with ice/water/chloroform
  4. customthe layers were separated
  5. extractionThe aqueous phase was extracted with chloroform (3×)
  6. washthe combined organic extracts were washed with saturated aqueous sodium bicarbonate (1×) and water (1×)
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-25f6ddba89fc48ffbe329a4bb13837dd
Source dataset
uspto-grants-2005_03
Patent number
US06869943B2

Reaction notes

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