Water → HCID 54527736, compound

HRID 1784678Notes

Reaction equation

HRID 1784678 reaction equation
Cl[C:2]1[N:7]([CH3:8])[C:6](=[O:9])[CH:5]=[C:4]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[N:3]=1.C(N(C(C)C)CC)(C)C.O>CN(C)C=O>[CH3:8][N:7]1[C:6](=[O:9])[CH:5]=[C:4]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 81531DiisopropylethylamineHCID 112760814(3H)-Pyrimidinone, 2-chloro-3-methyl-6-(4-pyridinyl)-

Product 1

HCID 54527736HCID 54527736, compoundYield 160.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2S-(4-bromophenyl)-4-benzyloxycarbonyl-piperazine (788 mg, 2.10 mmol), 2-chloro-3-methyl-6-(4-pyridyl)-pyrimidine-4-one (444 mg, 2.00 mmol) and diisopropylethylamine (0.70 mL, 4.00 mmol) in dimethylformamide (20 mL) was stirred at 80° C. for 3 h. The reaction mixture was poured into water and the whole was extracted with ethyl acetate. The organic layer was washed with brine, dried and concentrated in vacuo. Chromatographic purification of the residue provided 2-(2S-(4-bromophenyl)-4-benzyloxycarbonyl-piperazin-1-yl)}-3-methyl-6-pyridin-4-yl-3H-pyrimidin-4-one (601 mg, 54%). 1H NMR (300 MHz, CDCl3), δ 3.05(1H, m), 3.30-3.48(3H, m), 3.64(3H, s), 4.08-4.22(2H, m), 4.68(1H, m), 5.15(1H, d, J=12.3 Hz), 5.21(1H, d, J=12.6 Hz), 6.63(1H, s), 7.21(2H, d, J=8.4 Hz), 7.28-7.39(7H, m), 7.59(2H, d, J=6.3 Hz), 8.68(2H, d, J=6.3 Hz).

Workup

  1. extractionthe whole was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customChromatographic purification of the residue

Sources & evidence

ORD record
ord-d30735954690405681598bb28dc295f4
Source dataset
uspto-grants-2009_03
Patent number
US07504411B2

Reaction notes

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