Hydrochloric Acid → 3-(3-buten-1-yl)-8-chloro-3,7-dihydro-1H-purine-2,6-dione

HRID 2234969

反応式

HRID 2234969 の反応式
[Cl:1][C:2]1[NH:10][C:9]2[C:8](=[O:11])[NH:7][C:6](=[O:12])[NH:5][C:4]=2[N:3]=1.C(=O)([O-])[O-].[Na+].[Na+].Br[CH2:20][CH2:21][CH:22]=[CH2:23].N1CCOCC1.Cl>CN(C=O)C.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.CCOC(C)=O>[CH2:23]([N:5]1[C:4]2[N:3]=[C:2]([Cl:1])[NH:10][C:9]=2[C:8](=[O:11])[NH:7][C:6]1=[O:12])[CH2:22][CH:21]=[CH2:20]

参加物

9

反応物 5

HCID 313Hydrochloric AcidHCID 8083MorpholineHCID 10340Sodium CarbonateHCID 21241Homoallyl bromideHCID 261038-Chloroxanthine

生成物 1

HCID 112419373-(3-buten-1-yl)-8-chloro-3,7-dihydro-1H-purine-2,6-dione

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

8-chloro-3,7-dihydro-1H-purine-2,6-dione (100 mg, 0.44 mmol) was stirred with sodium carbonate (52 mg, 0.49 mmol) in dry DMF (3 ml) for 45 min., then 4-bromo-1-butene (66 mg, 0.49 mmol) was added and the mixture was stirred under nitrogen at 40 C for 65 h. After cooling to room temperature, the mixture was thoroughly degassed by evacuating the vessel and refilling with nitrogen several times. Tetrakis(triphenylphosphine)palladium(0) (102 mg, 0.09 mmol) was added, the mixture degassed again and then morpholine (0.385 ml, 4.4 mmol) added and stirring continued for 6.5 h. 2M HCl and EtOAc were added, and the 2-phase system was filtered to remove a yellow precipitated solid. The organic phase of the filtrate was separated and evaporated. The residue was dissolved with warming in THF-MeOH (1:1) and loaded onto an aminopropyl SPE (5 g) which was eluted with THF-MeOH (1:1) followed by MeOH and then 5% AcOH in MeOH-DCM (1:1). The product fraction was further purified by mass-directed autoprep to afford the title compound.

後処理

  1. customthe mixture was thoroughly degassed
  2. customby evacuating the vessel
  3. customthe mixture degassed again
  4. stirringstirring
  5. waitcontinued for 6.5 h
  6. filtrationthe 2-phase system was filtered
  7. customto remove
  8. customa yellow precipitated solid
  9. customThe organic phase of the filtrate was separated
  10. customevaporated
  11. dissolutionThe residue was dissolved
  12. temperaturewith warming in THF-MeOH (1:1)
  13. washwas eluted with THF-MeOH (1:1)
  14. customThe product fraction was further purified by mass-directed autoprep

出典と根拠

ORDレコード
ord-be3a4ece0a60448794ac8826b8991bb3
出典データセット
uspto-grants-2010_05
特許番号
US07713982B2

関連ノート

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