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

HRID 12749

反応式

HRID 12749 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.[F:23][C:24]1[C:29](B(O)O)=[CH:28][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:29]2[C:24]([F:23])=[N:25][CH:26]=[CH:27][CH:28]=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 27832702-Fluoropyridine-3-boronic acidHCID 589941523-Benzoyl-1-(4-chloro-butyl)-5-iodo-1H-pyrimidine-2,4-dione

生成物 1

HCID 451178293-Benzoyl-1-(4-chloro-butyl)-5-(2-fluoro-pyridin-3-yl)-1H-pyrimidine-2,4-dione収率 54.3%

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 (Prep129, 614 mg, 1.42 mmol) was dissolved in degassed DME-water solution (5-1, 35 ml). 2-Fluoro-pyridine 3-boronic acid (250 mg, 1.77 mmol), Na2CO3 (301 mg, 2.84 mmol), 2-(dicyclohexylphosphino)biphenyl (99 mg, 0.28 mmol) and Pd(PPh3)4 (328 mg, 0.28 mmol) were added and the mixture was refluxed for 3 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 (0.9 g, yellow oil) was purified by flash chromatography with ethyl acetate-petroleum ether (1-1) to give the title compound as yellow oil (310 mg, 54% yield).

後処理

  1. temperaturethe mixture was refluxed for 3 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 (0.9 g, yellow oil) was purified by flash chromatography with ethyl acetate-petroleum ether (1-1)

出典と根拠

ORDレコード
ord-f36738d46a914d64adcb7ef95c50ccd4
出典データセット
uspto-grants-2010_06
特許番号
US07727988B2

関連ノート

読み込み中…