1,4-Dioxane → 5,6,7,8-Tetrahydro-6-(5-methylpyridin-2-yl)pyrido[4,3-d]pyrimidin-4(3H)-one

HRID 19653

反応式

HRID 19653 の反応式
[N:1]1[C:6]2[CH2:7][CH2:8][NH:9][CH2:10][C:5]=2[C:4](=[O:11])[NH:3][CH:2]=1.Cl[C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][N:14]=1.O1CCOCC1.CN(C)C(=O)C>C(Cl)(Cl)Cl.CC(O)C>[CH3:19][C:16]1[CH:17]=[CH:18][C:13]([N:9]2[CH2:8][CH2:7][C:6]3[N:1]=[CH:2][NH:3][C:4](=[O:11])[C:5]=3[CH2:10]2)=[N:14][CH:15]=1

参加物

6

反応物 4

HCID 312751,4-DioxaneHCID 31374DimethylacetamideHCID 5813932-Chloro-5-methyl-pyridineHCID 1356276285,6,7,8-Tetrahydropyrido[4,3-d]pyrimidin-4(3H)-one

生成物 1

HCID 1359789575,6,7,8-Tetrahydro-6-(5-methylpyridin-2-yl)pyrido[4,3-d]pyrimidin-4(3H)-one収率 48.5%

試薬・触媒・溶媒 1

HCID 21906603Chloroform isopropyl alcohol溶媒

反応条件

温度
150 °C

実験手順

Into a 20 ml microwave tube was combined 5,6,7,8-Tetrahydro-3H-pyrido[4,3-d]pyrimidin-4-one (0.280 g, 0.00183 mol), 2-chloro-5-methylpyridine (0.47 g, 0.0037 mol), 1,4-dioxane (2.5 mL, 0.032 mol) N,N-diisopropylethylamine (0.64 mL, 0.0037 mol) and N,N-dimethylacetamide (0.5 mL, 0.005 mol). The mixture was heated via microwave at 150° C. for 4 hours. The mixture was reduced in vacuo and taken up in chloroform:IPA (3:1) (50 ml). The organic was washed with sodium bicarbonate and brine (1×50 ml), dried over sodium sulfate, and reduced in vacuo. The mixture was purified by flash chromatography on silica gel using a methylene chloride:methanol (0-10%) gradient. The combined pure fractions were reduced in vacuo to yield a bright yellow solid (0.215 g, 47.9%).

後処理

  1. customInto a 20 ml microwave tube was combined
  2. washThe organic was washed with sodium bicarbonate and brine (1×50 ml)
  3. dry with materialdried over sodium sulfate
  4. customThe mixture was purified by flash chromatography on silica gel using a methylene chloride

出典と根拠

ORDレコード
ord-f5fb789182c64475b71a7962bb9ce2e6
出典データセット
uspto-grants-2010_06
特許番号
US07745451B2

関連ノート

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