Iodoethane → 2-amino-6-(2,6-dichlorophenyl)-8-ethyl-7H,8H-pyrido[2,3-d]pyrimidin-7-one

HRID 53633

반응식

HRID 53633 반응식
[H-].[Na+].[NH2:3][C:4]1[N:5]=[CH:6][C:7]2[CH:13]=[C:12]([C:14]3[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:15]=3[Cl:21])[C:11]([OH:22])=[N:10][C:8]=2[N:9]=1.[CH2:23](I)[CH3:24]>CN(C)C=O>[NH2:3][C:4]1[N:5]=[CH:6][C:7]2[CH:13]=[C:12]([C:14]3[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:15]=3[Cl:21])[C:11](=[O:22])[N:10]([CH2:23][CH3:24])[C:8]=2[N:9]=1

참가 물질

5

반응물 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 178418283HCID 178418283, 화합물

생성물 1

HCID 53286252-amino-6-(2,6-dichlorophenyl)-8-ethyl-7H,8H-pyrido[2,3-d]pyrimidin-7-one수율 55.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
50 °C

실험 절차

To a suspension of NaH (60% in mineral oil, 27 mg) in 5 mL of dimethylformamide was added 2-amino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]-pyrimidin-7(8H)-one (172 mg, .56 mmol) from Example 11. The mixture was heated at 50° C. for 1 hour resulting in a clear solution. Ethyl iodine (60 μL, 0.75 mmol) was added, and the solution was stirred at 50° C. for 3.5 hours, cooled to room temperature, and poured into 30 mL of ice water. The resulting precipitate was removed by filtration and partitioned between ethyl acetate and water. The organic layer was separated and dried over MgSO4, filtered, and concentrated in vacuo. Flash chromatography, eluting with ethyl acetate, provided 104 mg (55%) of 2-amino-6-(2,6-dichlorophenyl)-8-ethyl-pyrido[2,3-d]-pyrimidin-7(8H)-one, mp 207°-209° C.

후처리

  1. customresulting in a clear solution
  2. temperaturecooled to room temperature
  3. customThe resulting precipitate was removed by filtration
  4. custompartitioned between ethyl acetate and water
  5. customThe organic layer was separated
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. washFlash chromatography, eluting with ethyl acetate

출처 및 근거

ORD 기록
ord-307bea7981354030a5e740ed4870d20f
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05620981

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