碳酸氢铯 → 4-[1-(4-methoxybenzyl)-3-(3-nitrophenyl)-1H-pyrazol-4-yl]-2-(methylsulfanyl)-pyrimidine

HRID 45882

反应方程式

HRID 45882 反应方程式
[CH3:1][O:2][C:3]1[CH:32]=[CH:31][C:6]([CH2:7][N:8]2[CH:12]=[C:11](B3OC(C)(C)C(C)(C)O3)[C:10]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([N+:28]([O-:30])=[O:29])[CH:23]=3)=[N:9]2)=[CH:5][CH:4]=1.[CH3:33][S:34][C:35]1[N:40]=[C:39](Cl)[CH:38]=[CH:37][N:36]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.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>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:37]3[CH:38]=[CH:39][N:40]=[C:35]([S:34][CH3:33])[N:36]=3)[C:10]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([N+:28]([O-:30])=[O:29])[CH:23]=3)=[N:9]2)=[CH:31][CH:32]=1

参与物

7

反应物 3

HCID 10796碳酸氢铯HCID 971132-甲硫基-4-氯嘧啶HCID 671842181-(4-methoxybenzyl)-3-(3-nitrophenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

产物 1

HCID 671844974-[1-(4-methoxybenzyl)-3-(3-nitrophenyl)-1H-pyrazol-4-yl]-2-(methylsulfanyl)-pyrimidine收率 88.4%

试剂、催化剂与溶剂 3

HCID 178418397HCID 178418397，化合物催化剂HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂HCID 312751,4-二氧六环溶剂

反应条件

温度
100 °C

实验过程

2.6 g (6 mmol) of 1-(4-methoxybenzyl)-3-(3-nitrophenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole were dissolved in a mixture of 520 ml of dioxane and 130 ml of water under a nitrogen atmosphere. 709 μl (6 mmol) of 2-methylthio-4-chloro-pyrimidine, 3.9 g (12 mmol) of cesium carbonate and 650 mg (0.6 mmol) of palladium tetrakis were added consecutively to the resulting solution under stirring. The reaction mixture was heated at 100° C. for 6 hours, then filtered through a celite pad and concentrated under reduced pressure. The residue was partitioned between dichloromethane and water, the organic layer dried over sodium sulphate and evaporated to dryness. The crude was finally purified by flash-chromatography on a silica gel column (cyclohexane-ethylacetate; from 9/1 to 4/1), giving 2.3 g (88%) of the title compound.

后处理

  1. filtrationfiltered through a celite pad
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was partitioned between dichloromethane and water
  4. dry with materialthe organic layer dried over sodium sulphate
  5. customevaporated to dryness
  6. customThe crude was finally purified by flash-chromatography on a silica gel column (cyclohexane-ethylacetate; from 9/1 to 4/1)

来源与证据

ORD记录
ord-2a0c45972ff64086aae7c712c118bf0e
来源数据集
uspto-grants-2013_09
专利号
US08541575B2

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