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1,8-Diazabicyclo(5.4.0)undec-7-ene → 2-Chloro-4-propyl-6-[4-(3-trifluoromethoxyphenyl)-imidazol-1-yl]-pyrimidine

HRID 1822788
ノート
印刷プレビュー

反応式

HRID 1822788 の反応式
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4]([CH2:9][CH2:10][CH3:11])[N:3]=1.[F:12][C:13]([F:27])([F:26])[O:14][C:15]1[CH:16]=[C:17]([C:21]2[N:22]=[CH:23][NH:24][CH:25]=2)[CH:18]=[CH:19][CH:20]=1.N12CCCN=C1CCCCC2>CN(C)C=O.O>[Cl:8][C:6]1[CH:5]=[C:4]([CH2:9][CH2:10][CH3:11])[N:3]=[C:2]([N:24]2[CH:25]=[C:21]([C:17]3[CH:18]=[CH:19][CH:20]=[C:15]([O:14][C:13]([F:12])([F:26])[F:27])[CH:16]=3)[N:22]=[CH:23]2)[N:7]=1.[Cl:1][C:2]1[N:3]=[C:4]([CH2:9][CH2:10][CH3:11])[CH:5]=[C:6]([N:24]2[CH:25]=[C:21]([C:17]3[CH:18]=[CH:19][CH:20]=[C:15]([O:14][C:13]([F:12])([F:26])[F:27])[CH:16]=3)[N:22]=[CH:23]2)[N:7]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2460112,4-Dichloro-6-propylpyrimidineHCID 178506377HCID 178506377、化合物

生成物 2

HCID 221700264-Chloro-6-propyl-2-[4-(3-trifluoromethoxyphenyl)-imidazol-1-yl]-pyrimidineHCID 221700392-Chloro-4-propyl-6-[4-(3-trifluoromethoxyphenyl)-imidazol-1-yl]-pyrimidine収率 58.8%

試薬・触媒・溶媒

2
HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 2,4-dichloro-6-propyl-pyrimidine (0.15 g) and 4-(3-trifluoromethoxy-phenyl)-1H-imidazole (0.2 g) in N,N-dimethylformamide (10 mL) was added 1,8-diazabicyclo[5.4.0]undec-7-ene (0.18 mL). After stirring at room temperature overnight, the solution was taken up in water and extracted three times with ethyl acetate. The ethyl acetate layers were combined washed twice with brine, dried over magnesium sulfate, and the volatiles were removed in vacuo. The resulting oil was purified on silica gel using 20% ethyl acetate/hexanes as the mobile phase to yield 4-chloro-6-propyl-2-[4-(3-trifluoromethoxyphenyl)-imidazol-1-yl]-pyrimidine (72.5 mg, first eluting regioisomer, ESI-MS (m/z) 383.3/385.2 [M+H]+, and 2-chloro-4-propyl-6-[4-(3-trifluoromethoxyphenyl)-imidazol-1-yl]-pyrimidine (88.4 mg, second eluting regioisomer).

後処理

  1. extractionextracted three times with ethyl acetate
  2. washThe ethyl acetate layers were combined washed twice with brine
  3. dry with materialdried over magnesium sulfate
  4. customthe volatiles were removed in vacuo
  5. customThe resulting oil was purified on silica gel using 20% ethyl acetate/hexanes as the mobile phase

出典と根拠

ORDレコード
ord-f0e1ed45bded44c08fdb96d7581fff3d
出典データセット
uspto-grants-2006_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07037916B2

反応ノート

読み込み中…

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