Sodium Cyanide → 3-Cyanopropyl 2-(indan-2-ylamino)-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylate

HRID 870600노트

반응식

HRID 870600 반응식
[C-:1]#[N:2].[Na+].[CH2:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH:5]1[NH:13][C:14]1[N:15]=[CH:16][C:17]2[CH2:22][N:21]([C:23]([O:25][CH2:26][CH2:27][CH2:28]Cl)=[O:24])[CH2:20][C:18]=2[N:19]=1>CN(C)C=O.ClCCl.O.[Cl-].[Li+]>[CH2:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH:5]1[NH:13][C:14]1[N:15]=[CH:16][C:17]2[CH2:22][N:21]([C:23]([O:25][CH2:26][CH2:27][CH2:28][C:1]#[N:2])=[O:24])[CH2:20][C:18]=2[N:19]=1

참가 물질

7

반응물 2

HCID 8929Sodium CyanideHCID 867265623-Chloropropyl 2-(indan-2-ylamino)-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylate

생성물 1

HCID 867265663-Cyanopropyl 2-(indan-2-ylamino)-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylate수율 87.6%

시약·촉매·용매 4

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매HCID 433294Lithium Chloride용매

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온도
100 °C

실험 절차

Add sodium cyanide (0.230 g; 1.5 equiv; 4.69 mmoles) to a solution containing 3-chloropropyl 2-(indan-2-ylamino)-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylate (1.15 g; 1.0 equiv; 3.08 mmoles) in dimethylformamide (10 mL). Heat the reaction mixture to 100° C. for 3 hours, then cool to ambient temperature, dilute with dichloromethane, water, and 5% lithium chloride solution. Separate the layers and further extract the aqueous layer with dichloromethane and ethyl acetate. Dry the combined organic extracts over sodium sulfate, filter, and concentrate to provide 3-cyanopropyl 2-(indan-2-ylamino)-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylate (0.98 g; 87%) as a brown solid: MS (m/z): 364(M+1).

후처리

  1. temperaturecool to ambient temperature
  2. customSeparate the layers
  3. extractionfurther extract the aqueous layer with dichloromethane and ethyl acetate
  4. dry with materialDry the combined organic extracts over sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate

출처 및 근거

ORD 기록
ord-6e61a4b9f9f941f98265ba7396cab2c5
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08969555B2

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