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

HRID 2400105

反応式

HRID 2400105 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-b90d5da9bb994eaa9e77be86ea5132d6
出典データセット
uspto-grants-1995_09
特許番号
US05453414

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