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

HRID 2203391ノート

反応式

HRID 2203391 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
107 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-982ce120367c45d29a4bd3aa2ed2ff8e
出典データセット
uspto-grants-2016_06
特許番号
US09365574B2

反応ノート

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