Pyridine → 6-dimethylaminocarbonyl-5-methyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone

HRID 2400105

반응식

HRID 2400105 반응식
[C:1]([C:4]1[N:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:7]([CH2:16][C:17]#[CH:18])[C:6](=[O:19])[C:5]=1[CH3:20])([OH:3])=O.Cl.[CH3:22][NH:23][CH3:24].N1C=CC=CC=1.C1(N=C=NC2CCCCC2)CCCCC1>C1COCC1>[CH3:22][N:23]([CH3:24])[C:1]([C:4]1[N:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:7]([CH2:16][C:17]#[CH:18])[C:6](=[O:19])[C:5]=1[CH3:20])=[O:3]

참가 물질

6

반응물 4

HCID 1049PyridineHCID 10473Dimethylamine, hydrochlorideHCID 10868DicyclohexylcarbodiimideHCID 196907156-carboxy-5-methyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone

생성물 1

HCID 196906856-dimethylaminocarbonyl-5-methyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone수율 32%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of 0.87 g (3.2 mmol) of crude 6-carboxy-5-methyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone, 0.32 g (3.9 mmol) of dimethylamine hydrochloride and 2 mL of pyridine in 10 mL of THF was added 0.74 g (3.6 mmol) of solid N,N'-dicyclohexylcarbodiimide. The mixture was stirred at room temperature for 4 days and filtered to remove insoluble material. The filtrate was diluted with 150 mL of ethyl acetate, washed with 50 mL of 5% aqueous HCl and 50 mL of saturated aqueous sodium bicarbonate and dried over MgSO4. Removal of the solvent left 0.40 g of crude product which was purified by flash chromatography on a 30 g column of silica gel, eluted with 60, 80 and 100% ethyl acetate in hexanes to furnish 0.30 g (32%) of 6-dimethylaminocarbonyl-5-methyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone (compound 19), mp 137°-140 ° C. 1H-NMR (CDCl3)δ2.15(3H,s), 2.40(1H, t), 3.00(3H,s), 3.10(3H,s), 4.65(2H,d), 7.55(3H,m), 7.70 (2H,m).

후처리

  1. filtrationfiltered
  2. customto remove insoluble material
  3. additionThe filtrate was diluted with 150 mL of ethyl acetate
  4. washwashed with 50 mL of 5% aqueous HCl and 50 mL of saturated aqueous sodium bicarbonate
  5. dry with materialdried over MgSO4
  6. customRemoval of the solvent
  7. waitleft 0.40 g of crude product which
  8. customwas purified by flash chromatography on a 30 g column of silica gel
  9. washeluted with 60, 80 and 100% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-b90d5da9bb994eaa9e77be86ea5132d6
출처 데이터셋
uspto-grants-1995_09
특허 번호
US05453414

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