Phthaloyl chloride → 9-Benzyloxy-6-phthalimidopurine

HRID 373895

Reaktionsgleichung

Reaktionsgleichung von HRID 373895
[C:1](Cl)(=[O:11])[C:2]1[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=1)[C:4](Cl)=[O:5].[CH2:13]([O:20][N:21]1[CH:29]=[N:28][C:27]2[C:22]1=[N:23][CH:24]=[N:25][C:26]=2[NH2:30])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(N(CC)CC)C>CN(C)C1C=CN=CC=1.O1CCCC1>[CH2:13]([O:20][N:21]1[CH:29]=[N:28][C:27]2[C:22]1=[N:23][CH:24]=[N:25][C:26]=2[N:30]1[C:4](=[O:5])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]2[C:1]1=[O:11])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Komponenten

6

Edukt 3

HCID 6955Phthaloyl chlorideHCID 8471TriethylamineHCID 123544939-(Benzyloxy)-9H-purin-6-amine

Produkt 1

HCID 145239699-Benzyloxy-6-phthalimidopurineAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Phthaloyl dichloride (13.35 g; 92.2 mmol) was added to a cooled solution of 9-benzyloxyadenine (14.9 g, 61.5 mmol), 4-dimethylaminopyridine (1.5 g, 12.3 mmol) and triethylamine (25.7 ml, 184.4 mmol) in tetrahydrofuran (200 ml). After 1 hour at room temperature the solvent was removed under reduced pressure and the residue partitioned between chloroform (500 ml) and saturated potassium bicarbonate (300 ml). The organic phase was separated, washed with water (200 ml), brine (200 ml), dried (MgSO4) and evaporated to dryness. Column chromatography on silica gel eluting with chloroform-methanol (100:1) afforded the title compound (11.20 g, 49%). IR: υmax (KBr) 3070, 1800, 1740, 1730, 1605, 1585, 1450 and 1410 cm-1 ; 1H NMR δH [(CD3)2SO] 5.70(2H, s, CH2Ph), 7.55(5H, s, CH2Ph), 8.20(4H, s, Ar), 8.95(1H, s, H-2), 9.25(1H, s, H-8). Found: C, 64.71; H, 3.78; N, 18.85%; m/z 371.1025. C20H13N5O3 requires: C, 64.68; H, 3.54; N, 18.86%; m/e 371.1018.

Aufarbeitung

  1. customAfter 1 hour at room temperature the solvent was removed under reduced pressure
  2. customthe residue partitioned between chloroform (500 ml) and saturated potassium bicarbonate (300 ml)
  3. customThe organic phase was separated
  4. washwashed with water (200 ml), brine (200 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-07fa810156e54e2b9a434faa8cb68b83
Quelldatensatz
uspto-grants-1992_11
Patentnummer
US05166198

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