Dimethylformamide → 4-((2-Amino-4-(mesitylsulfonyloxy)-6-methylpyrimidin-5-yl)methyl)-3-methoxyphenyl 2,4,6-trimethylbenzenesulfonate

HRID 2387852ノート

反応式

HRID 2387852 の反応式
[C:1]1([CH3:13])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[S:9](Cl)(=[O:11])=[O:10].[NH2:14][C:15]1[N:20]=[C:19]([OH:21])[C:18]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][C:24]=2[O:30][CH3:31])=[C:17]([CH3:32])[N:16]=1.CN(C=O)C>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:13][C:1]1[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[S:9]([O:29][C:26]1[CH:27]=[CH:28][C:23]([CH2:22][C:18]2[C:19]([O:21][S:9]([C:2]3[C:3]([CH3:8])=[CH:4][C:5]([CH3:7])=[CH:6][C:1]=3[CH3:13])(=[O:11])=[O:10])=[N:20][C:15]([NH2:14])=[N:16][C:17]=2[CH3:32])=[C:24]([O:30][CH3:31])[CH:25]=1)(=[O:11])=[O:10]

参加物

6

反応物 3

HCID 6228DimethylformamideHCID 130462-Mesitylenesulfonyl chloride2 回HCID 178493423HCID 178493423、化合物

生成物 1

HCID 866334084-((2-Amino-4-(mesitylsulfonyloxy)-6-methylpyrimidin-5-yl)methyl)-3-methoxyphenyl 2,4,6-trimethylbenzenesulfonate

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

2-Mesitylenesulfonyl chloride (5.25 g) was added to a mixture of the product from step (iii) (5 g), TEA (7 ml) and DMAP (120 mg) in DCM (100 ml) and stirred at rt for 24 h. DMF (10 ml) was added and the mixture heated under reflux for 12 h. Another portion of 2-mesitylenesulfonyl chloride (2 g) was added and heated under reflux for a further 24 h. The mixture was partitioned between DCM/water, the organics separated, washed with aq NaHCO3 soln, brine, dried and evaporated under reduced pressure. The residue was triturated with ether/isohexane and filtered to afford the subtitle compound, 9.515 g.

後処理

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 12 h
  3. temperatureheated
  4. temperatureunder reflux for a further 24 h
  5. customThe mixture was partitioned between DCM/water
  6. washthe organics separated, washed with aq NaHCO3 soln
  7. dry with materialbrine, dried
  8. customevaporated under reduced pressure
  9. customThe residue was triturated with ether/isohexane
  10. filtrationfiltered

出典と根拠

ORDレコード
ord-1bd055ecd3ed4b7786f48ab196934caa
出典データセット
uspto-grants-2012_09
特許番号
US08268990B2

反応ノート

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