Sodium Carbonate → Methyl[2,6-dimethyl-4-[(2'-(1-tert-butyl-1H-tetrazol-5-yl)biphenyl-4-ylmethyl)amino]pyrimidin-5-yl]ketone

HRID 129020ノート

反応式

HRID 129020 の反応式
[CH3:1][C:2]([C:4]1[C:5]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17](Br)=[CH:16][CH:15]=2)=[N:6][C:7]([CH3:11])=[N:8][C:9]=1[CH3:10])=[O:3].[C:21]([N:25]1[C:29]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2B(O)O)=[N:28][N:27]=[N:26]1)([CH3:24])([CH3:23])[CH3:22].C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.O.CCO.CCOC(C)=O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:1][C:2]([C:4]1[C:5]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=3[C:29]3[N:25]([C:21]([CH3:24])([CH3:23])[CH3:22])[N:26]=[N:27][N:28]=3)=[CH:16][CH:15]=2)=[N:6][C:7]([CH3:11])=[N:8][C:9]=1[CH3:10])=[O:3]

参加物

9

反応物 3

HCID 10340Sodium CarbonateHCID 10688121Methyl(4-(4-bromobenzylamino)-2,6-dimethylpyrimidin-5-yl)ketoneHCID 109447112-[(1-tert-Butyl)-1H-tetrazol-5-yl]phenylboronic acid

生成物 1

HCID 11080952Methyl[2,6-dimethyl-4-[(2'-(1-tert-butyl-1H-tetrazol-5-yl)biphenyl-4-ylmethyl)amino]pyrimidin-5-yl]ketone収率 75.1%

試薬・触媒・溶媒 5

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 702Ethanol溶媒HCID 962Water溶媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a heated solution of methyl(4-(4-bromobenzylamino)-2,6-dimethylpyrimidin-5-yl)ketone (1.67 g, 5.00 mmol) and tetrakis(triphenylphosphine) palladium(0) (0.29 g, 0.25 mmol) in toluene (20 mL) was added a partial solution of 2-[(1-tert-butyl)-1H-tetrazol-5-yl]phenylboronic acid (1.50 g, 6.10 mmol) (prepared according to J. W. Ellingboe, et al. U.S. Pat. No. 5,149,699) and Na2CO3 (1.06 g, 10.00 mmol) in water (10 mL) and EtOH (5 mL) in several portions over 1 h. Heating was continued for 2.5 h. The mixture was diluted with EtOAc and the layers were separated. The organic phase was washed with 0.1N NaOH, brine, dried MgSO4) and concentrated. Purification by flash chromatography (40-50% EtOAc/hexane) and trituration with hexane gave 1.71 g (75% ) of product as a white solid. An analytical sample was recrystallized from ether, mp 131°-132° C.

後処理

  1. customprepared
  2. temperatureHeating
  3. customthe layers were separated
  4. washThe organic phase was washed with 0.1N NaOH, brine, dried MgSO4) and
  5. concentrationconcentrated
  6. customPurification by flash chromatography (40-50% EtOAc/hexane) and trituration with hexane

出典と根拠

ORDレコード
ord-ad0afdacb1bd44e8b4c99488789d760a
出典データセット
uspto-grants-1995_11
特許番号
US05466692

反応ノート

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