Sodium Carbonate → 3-Benzoyl-1-(4-chloro-butyl)-5-(2-methyl-pyridin-4-yl)-1H-pyrimidine-2,4-dione

HRID 12677

反応式

HRID 12677 の反応式
[C:1]([N:9]1[C:14](=[O:15])[C:13](I)=[CH:12][N:11]([CH2:17][CH2:18][CH2:19][CH2:20][Cl:21])[C:10]1=[O:22])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:23][C:24]1[CH:29]=[C:28](B(O)O)[CH:27]=[CH:26][N:25]=1.C([O-])([O-])=O.[Na+].[Na+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1>COCCOC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([N:9]1[C:14](=[O:15])[C:13]([C:28]2[CH:27]=[CH:26][N:25]=[C:24]([CH3:23])[CH:29]=2)=[CH:12][N:11]([CH2:17][CH2:18][CH2:19][CH2:20][Cl:21])[C:10]1=[O:22])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 10340Sodium CarbonateHCID 27342162-(Dicyclohexylphosphino)biphenylHCID 41926642-Methylpyridine-4-boronic acidHCID 589941523-Benzoyl-1-(4-chloro-butyl)-5-iodo-1H-pyrimidine-2,4-dione

生成物 1

HCID 589941843-Benzoyl-1-(4-chloro-butyl)-5-(2-methyl-pyridin-4-yl)-1H-pyrimidine-2,4-dione収率 25.1%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 18180031Water 1,2-dimethoxyethane溶媒

実験手順

3-Benzoyl-1-(4-chloro-butyl)-5-iodo-1H-pyrimidine-2,4-dione (Prep 44, 433 mg, 1 mmol) was dissolved in degassed DME-water solution (5-1, 30 mL). 2-methyl-pyridine 4-boronic acid (205 mg, 1.5 mmol), Na2CO3 (212 mg, 2 mmol), 2-(dicyclohexylphosphino)biphenyl (70 mg, 0.2 mmol) and Pd(PPh3)4 (231 mg, 0.2 mmol) were added and the mixture was refluxed for 6 hours. The solvents were evaporated under vacuum and the crude was partitioned between ethyl acetate and water. The organic phase was dried (Na2SO4) and evaporated; the crude was purified by flash chromatography with DCM-MeOH—NH4OH (98-2-0.2) and SCX cartridge washing with MeOH and eluting with MeOH/NH3 95:5 to give the title compound (100 mg, 25% yield).

後処理

  1. temperaturethe mixture was refluxed for 6 hours
  2. customThe solvents were evaporated under vacuum
  3. customthe crude was partitioned between ethyl acetate and water
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. customevaporated
  6. customthe crude was purified by flash chromatography with DCM-MeOH—NH4OH (98-2-0.2) and SCX cartridge
  7. washwashing with MeOH
  8. washeluting with MeOH/NH3 95:5

出典と根拠

ORDレコード
ord-cc0aaa571d0c426fad3879969ab473b0
出典データセット
uspto-grants-2010_06
特許番号
US07727988B2

関連ノート

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