Methanol → 8-(3,3,4,4,4-Pentafluorobutyl)imidazo[1,5-a]pyrimidine-6-carboximidamide

HRID 2203391노트

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HRID 2203391 반응식
[NH2:1][Al]CCl.[F:5][C:6]([F:24])([C:20]([F:23])([F:22])[F:21])[CH2:7][CH2:8][C:9]1[N:10]=[C:11]([C:18]#[N:19])[N:12]2[CH:17]=[CH:16][CH:15]=[N:14][C:13]=12.CO>C1(C)C=CC=CC=1>[F:24][C:6]([F:5])([C:20]([F:21])([F:23])[F:22])[CH2:7][CH2:8][C:9]1[N:10]=[C:11]([C:18](=[NH:1])[NH2:19])[N:12]2[CH:17]=[CH:16][CH:15]=[N:14][C:13]=12

참가 물질

5

반응물 3

HCID 887MethanolHCID 86678981Amino(chloro)methylaluminumHCID 866790298-(3,3,4,4,4-Pentafluorobutyl)imidazo[1,5-a]pyrimidine-6-carbonitrile

생성물 1

HCID 866790308-(3,3,4,4,4-Pentafluorobutyl)imidazo[1,5-a]pyrimidine-6-carboximidamide

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
107 °C

실험 절차

A solution of amino(chloro)methylaluminum (0.5 M in toluene, 18.13 mL, 9.06 mmol) was added quickly to a stirred solution of the intermediate from Step F (0.3006 g, 1.036 mmol) in toluene (12.63 mL) and the mixture was heated at 107° C. overnight. The reaction mixture was cooled to room temperature, MeOH was added and the mixture was stirred for 30 min. The reaction mixture was filtered through a plug of Celite™ (diatomaceous earth), washed through with 2M NH3 in MeOH and the filtrate was concentrated in vacuo to give the crude product. This was purified by flash chromatography using a DCM/MeOH (2 N NH3 in MeOH) gradient to afford the desired product, as a yellow solid. m/z=308.0 (M+H).

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationThe reaction mixture was filtered through a plug of Celite™ (diatomaceous earth)
  3. washwashed through with 2M NH3 in MeOH
  4. concentrationthe filtrate was concentrated in vacuo
  5. customto give the crude product
  6. customThis was purified by flash chromatography

출처 및 근거

ORD 기록
ord-982ce120367c45d29a4bd3aa2ed2ff8e
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09365574B2

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