Acetic Acid → 8-chloro-3-(4-fluorobutyl)-3,7-dihydro-1H-purine-2,6-dione

HRID 2234968노트

반응식

HRID 2234968 반응식
[Cl:1][C:2]1[N:10](CC=C)[C:9]2[C:8](=[O:14])[NH:7][C:6](=[O:15])[N:5]([CH2:16][CH2:17][CH2:18][CH2:19][F:20])[C:4]=2[N:3]=1.C(O)(=O)C.C1([SiH3])C=CC=CC=1>C(Cl)Cl.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>[Cl:1][C:2]1[NH:10][C:9]2[C:8](=[O:14])[NH:7][C:6](=[O:15])[N:5]([CH2:16][CH2:17][CH2:18][CH2:19][F:20])[C:4]=2[N:3]=1

참가 물질

6

반응물 3

HCID 176Acetic AcidHCID 12752PhenylsilaneHCID 592995518-chloro-3-(4-fluorobutyl)-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione

생성물 1

HCID 592995618-chloro-3-(4-fluorobutyl)-3,7-dihydro-1H-purine-2,6-dione수율 43%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 6344Dichloromethane용매

실험 절차

To a suspension of 8-chloro-3-(4-fluorobutyl)-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione (100 mg, 0.33 mmol, 1eq) in anhydrous DCM (2 ml) was added palladium tetrakis (38 mg, 0.033 mmol, 10% bw), followed by acetic acid (115 ul, 121 mg, 2.01 mmol, 6eq) and phenyl silane (410 ul, 360 mg, 3.33 mmol, 10eq). The resulting light yellow solution was stirred at ambient temperature for 16 h to give a dark purple solution. The solvent was removed under a stream of nitrogen and the residue dissolved in a DMSO/methanol solution (3 ml, 2:1) with heating. The gelatinous mixture was allowed to cool to ambient temperature, filtered then purified by mass directed autopreparative HPLC to give the title compound as a white solid (35 mg, 43%). m/z 261.2[MH+] NMR (400 MHz, MeOD), δH 4.45 (2H, dt, J=47 and 6 Hz), 4.03 (2H, t, J=7 Hz), 1.90-1.65 (4H, m).

후처리

  1. customto give a dark purple solution
  2. customThe solvent was removed under a stream of nitrogen
  3. dissolutionthe residue dissolved in a DMSO/methanol solution (3 ml, 2:1)
  4. temperaturewith heating
  5. temperatureto cool to ambient temperature
  6. filtrationfiltered
  7. customthen purified by mass

출처 및 근거

ORD 기록
ord-78c4f632467b4f5680ce1c91adeb4729
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07713982B2

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