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Diisopropylethylamine → 4-(6-methyl-2-pyridinyl)-1-(4-{(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}butyl)-2(1H)-pyrimidinone dihydrochloride

HRID 1514446
Notes
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Reaction equation

HRID 1514446 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[N:13]=2)=[N:8][C:7]1=[O:19].[F:20][C:21]([F:35])([F:34])[C:22]1[CH:27]=[CH:26][C:25]([C@:28]23[CH2:33][C@H:32]2[CH2:31][NH:30][CH2:29]3)=[CH:24][CH:23]=1.CCN(C(C)C)C(C)C>CCO>[ClH:1].[ClH:1].[CH3:18][C:14]1[N:13]=[C:12]([C:9]2[CH:10]=[CH:11][N:6]([CH2:5][CH2:4][CH2:3][CH2:2][N:30]3[CH2:31][C@H:32]4[C@:28]([C:25]5[CH:24]=[CH:23][C:22]([C:21]([F:20])([F:35])[F:34])=[CH:27][CH:26]=5)([CH2:33]4)[CH2:29]3)[C:7](=[O:19])[N:8]=2)[CH:17]=[CH:16][CH:15]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 592428011-(4-Chloro-butyl)-4-(6-methyl-pyridin-2-yl)-1H-pyrimidin-2-oneHCID 59337591(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexane

Product 1

HCID 686973904-(6-methyl-2-pyridinyl)-1-(4-{(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}butyl)-2(1H)-pyrimidinone dihydrochlorideYield 36.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1-(4-chloro-butyl)-4-(6-methyl-pyridin-2-yl)-1H-pyrimidin-2-one (Prep17, 48 mg, 0.17 mmol), (1S,5R)-1-(4-trifluoromethyl-phenyl)-3-aza-bicyclo[3.1.0]hexane (Prep4, 38 mg, 0.17 mmol), KI (2 mg) and DIPEA (66 mg, 0.51 mmol) in absolute EtOH (2 ml) was placed in a microwave oven and irradiated at 125° C. for 13 hours. The solvent was removed under vacuum and the residue was redissolved in DCM and filtered. The filtrate was stirred in the presence of PS-isocyanate (350 mg) for 3 hours. The mixture was filtered and the solvent removed under vacuum. The crude was purified by flash chromatography with DCM-MeOH—NH4OH (99-1-0.1) to give the title compound (17 mg, 4% yield) as a free base.

Workup

  1. customirradiated at 125° C. for 13 hours
  2. customThe solvent was removed under vacuum
  3. dissolutionthe residue was redissolved in DCM
  4. filtrationfiltered
  5. filtrationThe mixture was filtered
  6. customthe solvent removed under vacuum
  7. customThe crude was purified by flash chromatography with DCM-MeOH—NH4OH (99-1-0.1)

Sources & evidence

ORD record
ord-011686e4a1294291b5ab0e9ead0cc314
Source dataset
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08222266B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes