Triethylamine → HCID 67117441, compound

HRID 1784700Notes

Reaction equation

HRID 1784700 reaction equation
Cl.Cl.[O:3]1[CH:7]=[N:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]3[CH2:19][NH:18][CH2:17][CH2:16][NH:15]3)=[CH:10][CH:9]=2)=[N:4]1.C(N(CC)CC)C.Cl[C:28]1[N:33]([CH3:34])[C:32](=[O:35])[CH:31]=[C:30]([C:36]2[CH:41]=[CH:40][N:39]=[CH:38][CH:37]=2)[N:29]=1>O1CCCC1>[O:3]1[CH:7]=[N:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C@@H:14]3[NH:15][CH2:16][CH2:17][N:18]([C:28]4[N:33]([CH3:34])[C:32](=[O:35])[CH:31]=[C:30]([C:36]5[CH:37]=[CH:38][N:39]=[CH:40][CH:41]=5)[N:29]=4)[CH2:19]3)=[CH:10][CH:9]=2)=[N:4]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 112760814(3H)-Pyrimidinone, 2-chloro-3-methyl-6-(4-pyridinyl)-HCID 67117412HCID 67117412, compound

Product 1

HCID 67117441HCID 67117441, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 2-(4-(1,2,4-oxadiazol-3-yl)phenyl)piperazine dihydrochloride (102 mg, 0.34 mmol) in tetrahydrofuran (6 mL) was added triethylamine (0.23 mL, 1.65 mmol) and then 2-chloro-3-methyl-6-(4-pyridyl)-3H-pyrimidin-4-one (73 mg, 0.33 mmol) at room temperature. After stirring for 24 h, the resulting mixture was concentrated in vacuo. The residue was dissolved in dichloromethane and saturated sodium bicarbonate aqueous solution, and the solution was passed through CHEM ELUT CE1010 (manufactured by VARIAN). The filtrate was concentrated in vacuo to yield crystals, which were washed with diisopropyl ether and ethanol to afford (S)-2-(3-(4-(1,2,4-oxadiazol-3-yl)phenyl) piperazin-1-yl)-3-methyl-6-(4-pyridyl)pyrimidin-4-one (102 mg 74%) as a white powder.

Workup

  1. customat room temperature
  2. concentrationthe resulting mixture was concentrated in vacuo
  3. dissolutionThe residue was dissolved in dichloromethane
  4. concentrationThe filtrate was concentrated in vacuo
  5. customto yield crystals, which
  6. washwere washed with diisopropyl ether and ethanol

Sources & evidence

ORD record
ord-02640808f39546fa99ccda8cbe00e9f0
Source dataset
uspto-grants-2009_03
Patent number
US07504411B2

Reaction notes

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