Morpholine → 7-Benzyl-4-(morpholin-4-yl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine

HRID 8715Notes

Reaction equation

HRID 8715 reaction equation
[CH2:1]([N:8]1[CH2:17][CH2:16][C:15]2[C:14](Cl)=[N:13][CH:12]=[N:11][C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1>C(O)(C)C>[CH2:1]([N:8]1[CH2:17][CH2:16][C:15]2[C:14]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[N:13][CH:12]=[N:11][C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 219588387-Benzyl-4-chloro-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine

Product 1

HCID 219836347-Benzyl-4-(morpholin-4-yl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidineYield 100.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 7-benzyl-4-chloro-5,6,7,8-tetrahydro-pyrido[3,4-d]pyrimidine 4a (0.46 g, 1.77 mmol) in isopropanol (20 mL) was added morpholine (0.38 g, 4.42 mmol), and the reaction mixture was heated to reflux for 18 h. The solvent was removed in vacuo, and the residue was suspended in a saturated solution of NaHCO3, and the product was extracted with dichloromethane. The combined organic extracts were dried over MgSO4 and concentrated in vacuo to provide a residue, which was purified by chromatography to give 0.55 g of 7-benzyl-4-morpholin-4-yl-5,6,7,8-tetrahydro-pyrido[3,4-d]pyrimidine 5a as a pale yellow liquid.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 18 h
  3. customThe solvent was removed in vacuo
  4. extractionthe product was extracted with dichloromethane
  5. dry with materialThe combined organic extracts were dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customto provide a residue, which
  8. customwas purified by chromatography

Sources & evidence

ORD record
ord-519e79bd4d7445b0b453c00c46cc063d
Source dataset
uspto-grants-2006_08
Patent number
US07091200B2

Reaction notes

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