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

HRID 3234

반응식

HRID 3234 반응식
[H-].[Na+].[CH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[CH2:13][C:14]#[N:15].[CH2:16]([NH:18][C:19]1[C:24]([CH:25]=O)=[CH:23][N:22]=[C:21]([NH:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:20]=1)[CH3:17].O>C(OCCO)C>[CH2:16]([N:18]1[C:19]2[N:20]=[C:21]([NH:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[N:22]=[CH:23][C:24]=2[CH:25]=[C:13]([C:4]2[CH:5]=[CH:6][C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:3]=2)[C:14]1=[NH:15])[CH3:17]

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 820082-NaphthylacetonitrileHCID 108240804-Ethylamino-2-phenylamino-pyrimidine-5-carbaldehyde

생성물 1

HCID 11710876(8-Ethyl-7-imino-6-naphthalen-2-yl-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-yl)-phenylamine수율 82.4%

시약·촉매·용매 1

HCID 8076Glycol monoethyl ether용매

실험 절차

To a suspension of NaH (60% in mineral oil, 27 mg) in 5 mL of 2-ethoxyethanol was added 2-naphthyl-acetonitrile (227 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 110° C. for 1 hour, resulting in a dark brown solution. Upon cooling, the solution was poured into 30 mL of 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 400 mg (82%) of yellow solid, (8-ethyl-7-imino-6-naphthalen-2-yl-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-yl)-phenylamine; mp 236°-242° C.

후처리

  1. temperaturethe reaction heated at 110° C. for 1 hour
  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

출처 및 근거

ORD 기록
ord-5004f689fe8441b7b8fb304853ccbbc3
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05733914

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