Hydrochloric Acid → 6-(Tert-butoxycarbonyl)-3-propargyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-2,4-dione

HRID 1500605Notes

Reaction equation

HRID 1500605 reaction equation
C(O[C:4]([C:6]1[CH2:7][N:8]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:9][CH2:10][C:11]=1[NH:12][C:13]([O:15]C1C=CC=CC=1)=O)=[O:5])C.[CH2:29]([NH2:32])[C:30]#[CH:31].C1CCN2C(=NCCC2)CC1.NC(N)=O.[OH-].[Na+].Cl>C1COCC1>[C:25]([O:24][C:22]([N:8]1[CH2:9][CH2:10][C:11]2[NH:12][C:13](=[O:15])[N:32]([CH2:29][C:30]#[CH:31])[C:4](=[O:5])[C:6]=2[CH2:7]1)=[O:23])([CH3:26])([CH3:27])[CH3:28]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 1176UreaHCID 14798Sodium HydroxideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 239041PropargylamineHCID 66685805Ethyl-4-phenoxycarbonylamino-1-tert-butoxycarbonyl-1,2,5,6-tetrahydropyridine-3-carboxylate

Product 1

HCID 866631126-(Tert-butoxycarbonyl)-3-propargyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl-4-phenoxycarbonylamino-1-tert-butoxycarbonyl-1,2,5,6-tetrahydropyridine-3-carboxylate (5.0 g) was dissolved in THF (50 ml), and propargylamine (1.32 ml) and 1,8-diazabicyclo[5.4.0]-7-undecene (DBU) (0.2 ml) were added and the resultant mixture was stirred at room temperature for 2 hours. After production of an intermediate (urea) was confirmed by TLC, a 5 N aqueous sodium hydroxide solution (5 ml) was added and the resultant mixture was further stirred at room temperature for 2 hours. To the reaction solution, 6 N hydrochloric acid was added to neutralize and the resultant mixture was then concentrated. To the residue, water was added and the mixture was extracted with ethyl acetate. After the organic layer was washed with a saturated saline solution, the organic layer was dried over sodium sulfate, filtrated and concentrated under reduced pressure. A precipitate was obtained by filtration. The titled compound (3.78 g) was obtained as a white powder.

Workup

  1. concentrationthe resultant mixture was then concentrated
  2. additionTo the residue, water was added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washAfter the organic layer was washed with a saturated saline solution
  5. dry with materialthe organic layer was dried over sodium sulfate
  6. filtrationfiltrated
  7. concentrationconcentrated under reduced pressure
  8. customA precipitate was obtained by filtration

Sources & evidence

ORD record
ord-aee827a40f924f74985411118979f327
Source dataset
uspto-grants-2015_12
Patent number
US09206173B2

Reaction notes

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