1,8-Diazabicyclo(5.4.0)undec-7-ene → 8-({6-[4-(Trifluoromethyl)phenyl]pyrimidin-4-yl}oxy)quinolin-2-ol

HRID 858993Notes

Reaction equation

HRID 858993 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)[N:5]=[CH:4][N:3]=1.[N:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][C:26]=2[OH:28])[CH:21]=[CH:20][C:19]=1[OH:29].N12CCCN=C1CCCCC2>C(#N)C.CCOC(C)=O>[F:15][C:14]([F:17])([F:16])[C:11]1[CH:12]=[CH:13][C:8]([C:6]2[N:5]=[CH:4][N:3]=[C:2]([O:28][C:26]3[CH:25]=[CH:24][CH:23]=[C:22]4[C:27]=3[NH:18][C:19](=[O:29])[CH:20]=[CH:21]4)[CH:7]=2)=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 167478374-Chloro-6-(4-(trifluoromethyl)phenyl)pyrimidineHCID 178515617HCID 178515617, compound

Product 1

HCID 167482098-({6-[4-(Trifluoromethyl)phenyl]pyrimidin-4-yl}oxy)quinolin-2-ol

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 4-chloro-6-(4-trifluoromethyl-phenyl)-pyrimidine, (Example 2(a), Method A), (0.10 g, 0.39 mmol) and 2,8-quinolinediol (0.075 g, 0.46 mmol, Fluka) in acetonitrile (5 mL) was added 1,8-diazabicyclo[5.4.0]undec-7-ene (0.069 mL, 0.46 mmol, Aldrich). The mixture was heated to reflux for 6 h, allowed to cool to room temperature, and diluted with EtOAc. The solids were filtered, washed with EtOAc and dried in vacuum for 16 h to yield the title compound as long white needles. Mp: 312° C., MS (ESI, pos. ion) m/z: 384 (M+1).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 6 h
  3. filtrationThe solids were filtered
  4. washwashed with EtOAc
  5. customdried in vacuum for 16 h

Sources & evidence

ORD record
ord-0968306a51724d2598048087b48020a9
Source dataset
uspto-grants-2006_12
Patent number
US07148221B2

Reaction notes

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