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

HRID 1822788Notes

Reaction equation

HRID 1822788 reaction equation
[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

Participants

7

Reactant 3

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

Product 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]-pyrimidineYield 58.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-f0e1ed45bded44c08fdb96d7581fff3d
Source dataset
uspto-grants-2006_05
Patent number
US07037916B2

Reaction notes

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