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

HRID 1514445
ノート
印刷プレビュー

反応式

HRID 1514445 の反応式
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[CH:11]=[C:10]([CH3:12])[C:9]([C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=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.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[ClH:1].[CH3:12][C:10]1[C:9]([C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)=[N:8][C:7](=[O:19])[N:6]([CH2:5][CH2:4][CH2:3][CH2:2][N:30]2[CH2:31][C@H:32]3[C@:28]([C:25]4[CH:24]=[CH:23][C:22]([C:21]([F:20])([F:35])[F:34])=[CH:27][CH:26]=4)([CH2:33]3)[CH2:29]2)[CH:11]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 592427851-(4-Chloro-butyl)-5-methyl-4-pyridin-3-yl-1H-pyrimidin-2-oneHCID 59337591(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexane

生成物 1

HCID 687019445-methyl-4-(3-pyridinyl)-1-(4-{(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}butyl)-2(1H)-pyrimidinone hydrochloride収率 12%

試薬・触媒・溶媒 2

HCID 962
Water
溶媒
HCID 6228Dimethylformamide溶媒

実験手順

A solution of 1-(4-chloro-butyl)-5-methyl-4-pyridin-3-yl-1H-pyrimidin-2-one (Prep12, 86 mg, 0.31 mmol), (1S,5R)-1-(4-trifluoromethyl-phenyl)-3-aza-bicyclo[3.1.0]hexane (Prep4, 63 mg, 0.28 mmol), KI (2 mg) and K2CO3 (43 mg, 0.31 mmol) in DMF (2 ml) was placed in a microwave oven and irradiated at 115° C. for 1 hour. After cooling, the solution was diluted with water and extracted with ethyl acetate. The organic layer was washed with brine, dried (Na2SO4) and evaporated 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.

後処理

  1. customirradiated at 115° C. for 1 hour
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated The solvent
  7. customwas removed under vacuum
  8. dissolutionthe residue was redissolved in DCM
  9. filtrationfiltered
  10. filtrationThe mixture was filtered
  11. customthe solvent removed under vacuum
  12. customThe crude was purified by flash chromatography with DCM-MeOH—NH4OH (99-1-0.1)

出典と根拠

ORDレコード
ord-b12f4a8abae5457ea46f773074605b4c
出典データセット
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08222266B2

反応ノート

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