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

HRID 2234969

반응식

HRID 2234969 반응식
[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]

참가 물질

9

반응물 5

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

생성물 1

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

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-be3a4ece0a60448794ac8826b8991bb3
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07713982B2

연결된 노트

불러오는 중…