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

HRID 1943836노트

반응식

HRID 1943836 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, 1 eq) 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, 6 eq) and phenyl silane (410 ul, 360 mg, 3.33 mmol, 10 eq). 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-0f2108df81184c7db531a2196b2728ef
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08394808B2

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