Water → (8-Ethyl-7-imino-6-thiophen-3-yl-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-yl)-phenylamine

HRID 3224

反応式

HRID 3224 の反応式
[H-].[Na+].[S:3]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4]1.[CH2:11]([NH:13][C:14]1[C:19]([CH:20]=O)=[CH:18][N:17]=[C:16]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:15]=1)[CH3:12].O>C(OCCO)C>[CH2:11]([N:13]1[C:14]2[N:15]=[C:16]([NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[N:17]=[CH:18][C:19]=2[CH:20]=[C:8]([C:5]2[CH:6]=[CH:7][S:3][CH:4]=2)[C:9]1=[NH:10])[CH3:12]

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 837303-ThienylacetonitrileHCID 108240804-Ethylamino-2-phenylamino-pyrimidine-5-carbaldehyde

生成物 1

HCID 10736433(8-Ethyl-7-imino-6-thiophen-3-yl-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-yl)-phenylamine収率 78.9%

試薬・触媒・溶媒 1

HCID 8076Glycol monoethyl ether溶媒

実験手順

To a suspension of NaH (60% in mineral oil, 27 mg) in 5 mL of 2-ethoxyethanol was added 3-thiopheneacetonitrile (168 mg, 1.36 mmol). After stirring for 5 minutes at room temperature, 4-ethylamino-2-phenylamino-pyrimidine-5-carbaldehyde (300 mg, 1.24 mmol) was added, and the reaction heated at 120° C. for 2 hours, resulting in a dark brown solution. Upon cooling, the solution was poured into water which caused precipitation. The resulting precipitate was removed by filtration and washed with water. The crude product was purified by flash chromatography, eluting with 5% methanol/methylene chloride, followed by 10% methanol/methylene chloride. Concentration of product fractions yielded 340 mg (78%) of (8-ethyl-7-imino-6-thiophen-3-yl-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-yl)-phenylamine; mp 220°-222° C.

後処理

  1. temperaturethe reaction heated at 120° C. for 2 hours
  2. customresulting in a dark brown solution
  3. temperatureUpon cooling
  4. customprecipitation
  5. customThe resulting precipitate was removed by filtration
  6. washwashed with water
  7. customThe crude product was purified by flash chromatography
  8. washeluting with 5% methanol/methylene chloride

出典と根拠

ORDレコード
ord-5ac9e9c1c2b44b098f10a1ddc3f11428
出典データセット
uspto-grants-1998_03
特許番号
US05733914

関連ノート

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