Triethylamine → HCID 44540011, compound

HRID 1914624Notes

Reaction equation

HRID 1914624 reaction equation
Br.[NH2:2][CH2:3][CH:4]1[C:9]2=[N:10][C:11]([C:15]3[CH:20]=[CH:19][N:18]=[CH:17][N:16]=3)=[CH:12][C:13](=[O:14])[N:8]2[CH2:7][CH2:6][CH2:5]1.[Cl:21][C:22]1[CH:30]=[CH:29][C:25]([C:26](O)=[O:27])=[C:24]([O:31][CH3:32])[CH:23]=1.C(OP(C#N)(=O)OCC)C.C(N(CC)CC)C>CN(C)C=O.C(OCC)(=O)C.O>[Cl:21][C:22]1[CH:30]=[CH:29][C:25]([C:26]([NH:2][CH2:3][CH:4]2[C:9]3=[N:10][C:11]([C:15]4[CH:20]=[CH:19][N:18]=[CH:17][N:16]=4)=[CH:12][C:13](=[O:14])[N:8]3[CH2:7][CH2:6][CH2:5]2)=[O:27])=[C:24]([O:31][CH3:32])[CH:23]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 936824-Chloro-o-anisic acidHCID 67176912HCID 67176912, compound

Product 1

HCID 44540011HCID 44540011, compoundYield 57.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.067 g (0.20 mmol) of 9-aminomethyl-2-pyrimidin-4-yl-6,7,8,9-tetrahydro-pyrido[1,2-a]pyrimidin-4-one hydrobromide (1:1) dissolved in 2.00 mL of dimethylformamide were added 0.053 g (0.20 mmol) of 4-chloro-2-methoxy-benzoic acid, 0.030 mL (0.20 mmol) of diethylcyanophosphonate and 0.140 mL (1.00 mmol) of triethylamine. The resulting mixture was stirred at room temperature for 2 hours. Water and ethyl acetate were added, the mixture was extracted with ethyl acetate and the organic phase was washed with a saturated solution of ammonium chloride, dried over sodium sulfate and concentrated. A purification on silica gel (eluant: dichloromethane with 5% of methanol) gave 0.049 g (57%) of pure product obtained in the form of free base as a solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washthe organic phase was washed with a saturated solution of ammonium chloride
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customA purification on silica gel (eluant: dichloromethane with 5% of methanol)

Sources & evidence

ORD record
ord-7f7b12b6aec645bd8080992a9c2b8963
Source dataset
uspto-grants-2013_12
Patent number
US08614219B2

Reaction notes

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