Cesium carbonate → 6-(2-Methyl-5-nitro-phenyl)-2-[4-(4-methyl-piperazine-1-carbonyl)phenylamino]-7,8-dihydro-6H-pyrido[4,3-d]pyrimidin-5-one

HRID 2092590

反応式

HRID 2092590 の反応式
C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.I[C:44]1[CH:49]=[CH:48][C:47]([C:50]([N:52]2[CH2:57][CH2:56][N:55]([CH3:58])[CH2:54][CH2:53]2)=[O:51])=[CH:46][CH:45]=1.[NH2:59][C:60]1[N:61]=[CH:62][C:63]2[C:69](=[O:70])[N:68]([C:71]3[CH:76]=[C:75]([N+:77]([O-:79])=[O:78])[CH:74]=[CH:73][C:72]=3[CH3:80])[CH2:67][CH2:66][C:64]=2[N:65]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1>[CH3:80][C:72]1[CH:73]=[CH:74][C:75]([N+:77]([O-:79])=[O:78])=[CH:76][C:71]=1[N:68]1[CH2:67][CH2:66][C:64]2[N:65]=[C:60]([NH:59][C:44]3[CH:49]=[CH:48][C:47]([C:50]([N:52]4[CH2:57][CH2:56][N:55]([CH3:58])[CH2:54][CH2:53]4)=[O:51])=[CH:46][CH:45]=3)[N:61]=[CH:62][C:63]=2[C:69]1=[O:70]

参加物

6

反応物 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 8799091-(4-Iodobenzoyl)-4-methylpiperazineHCID 673291422-Amino-6-(2-methyl-5-nitro-phenyl)-7,8-dihydro-6H-pyrido[4,3-d]pyrimidin-5-one

生成物 1

HCID 673292106-(2-Methyl-5-nitro-phenyl)-2-[4-(4-methyl-piperazine-1-carbonyl)phenylamino]-7,8-dihydro-6H-pyrido[4,3-d]pyrimidin-5-one

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

A mixture of 4,5-Bis(diphenylphos-phino)-9,9-dimethylxanthene (xanthopos) (8.6 mg, 0.0148 mmol) and Tris(dibenzylideneacetone)dipalladium(0)[Pd2(dba)3] (6.81 mg, 0.0074 mmol) in dry 1,4-dioxane (5 ml) was stirred vigorously and nitrogen was bubbled through the suspension for 30 minutes. (4-Iodo-phenyl)-(4-methyl-piperazin-1-yl)-methanone (41.1 mg, 0.1247 mmol), 2-Amino-6-(2-methyl-5-nitro-phenyl)-7,8-dihydro-6H-pyrido[4,3-d]pyrimidin-5-one (37.3 mg, 0.1247 mmol) and dry cesium carbonate (100 mg, 0.31 mmol) was added. Nitrogen was bubbled through for another 30 minutes; the mixture was allowed to reflux overnight. The mixture was cooled, diluted with ethylacetate, water was added and the layers were separated. The aqueous layer was extracted with ethyl acetate and the two organic extracts were combined. The organics were washed with brine, then dried (sodium sulfate), filtered and concentrated. Silica gel chromatography using 5-10% ethyl acetate/hexane as eluent provided 6-(2-Methyl-5-nitro-phenyl)-2-[4-(4-methyl-piperazine-1-carbonyl)phenylamino]-7,8-dihydro-6H-pyrido[4,3-d]pyrimidin-5-one [22] as a yellow solid [Yield: 12.3 mg, 19.7%]

後処理

  1. customnitrogen was bubbled through the suspension for 30 minutes
  2. customNitrogen was bubbled through for another 30 minutes
  3. temperatureto reflux overnight
  4. temperatureThe mixture was cooled
  5. additiondiluted with ethylacetate, water
  6. additionwas added
  7. customthe layers were separated
  8. extractionThe aqueous layer was extracted with ethyl acetate
  9. washThe organics were washed with brine
  10. dry with materialdried (sodium sulfate)
  11. filtrationfiltered
  12. concentrationconcentrated

出典と根拠

ORDレコード
ord-d869da951e7a47728154d249a8a8d105
出典データセット
uspto-grants-2013_05
特許番号
US08440679B2

関連ノート

読み込み中…