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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
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HRID 1822788 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

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

생성물 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]-pyrimidine수율 58.8%

시약·촉매·용매

2
HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-f0e1ed45bded44c08fdb96d7581fff3d
출처 데이터셋
uspto-grants-2006_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07037916B2

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