Sodium hydride → (6-Iodo-pyrimidin-4-yl)-(8-methyl-2,3-dihydro-benzo[1,4]dioxin-6-yl)-methanone

HRID 469363ノート

反応式

HRID 469363 の反応式
[H-].[Na+].[I:3][C:4]1[CH:9]=[C:8](I)[N:7]=[CH:6][N:5]=1.[CH3:11][C:12]1[C:17]2[O:18][CH2:19][CH2:20][O:21][C:16]=2[CH:15]=[C:14]([CH:22]=[O:23])[CH:13]=1.[Cl-].C[N+]1C=CN(C)C=1>C1COCC1>[I:3][C:4]1[N:5]=[CH:6][N:7]=[C:8]([C:22]([C:14]2[CH:13]=[C:12]([CH3:11])[C:17]3[O:18][CH2:19][CH2:20][O:21][C:16]=3[CH:15]=2)=[O:23])[CH:9]=1

参加物

6

反応物 4

HCID 24758Sodium hydrideHCID 110624321,3-Dimethylimidazolium ChlorideHCID 157602954,6-DiiodopyrimidineHCID 451220228-Methyl-2,3-dihydro-1,4-benzodioxin-6-carbaldehyde

生成物 1

HCID 58181192(6-Iodo-pyrimidin-4-yl)-(8-methyl-2,3-dihydro-benzo[1,4]dioxin-6-yl)-methanone

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

0.131 g (3.00 mmol) sodium hydride (55%, suspension in mineral oil) were added to 0.677 g (2.00 mmol) 4,6-diiodopyrimidine, 0.535 g (3.00 mmol) 8-methyl-2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde (US2005/256099) and 0.133 g (1.00 mmol) 1,3-dimethylimidazolium chloride in 10 mL THF and the mixture was refluxed for 4 h. Then the reaction mixture was mixed with ice water and extracted with EtOAc. The organic phase was dried on sodium sulphate, evaporated down i. vac. and the residue was purified by preparative HPLC-MS. The fractions containing the product were combined and the organic solvent was evaporated down i. vac. The residue was made alkaline with 1N aqueous sodium hydroxide solution and the grease precipitated was extracted with EtOAc. The organic phase was dried on sodium sulphate, filtered, evaporated down and dried i. vac.

後処理

  1. temperaturethe mixture was refluxed for 4 h
  2. extractionextracted with EtOAc
  3. customThe organic phase was dried on sodium sulphate
  4. customevaporated down i
  5. customand the residue was purified by preparative HPLC-MS
  6. additionThe fractions containing the product
  7. customthe organic solvent was evaporated down i
  8. customthe grease precipitated
  9. extractionwas extracted with EtOAc
  10. customThe organic phase was dried on sodium sulphate
  11. filtrationfiltered
  12. customevaporated down
  13. customdried i

出典と根拠

ORDレコード
ord-4b7060ab492f473caa210b3eb2b9c648
出典データセット
uspto-grants-2014_01
特許番号
US08629137B2

反応ノート

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