Methanol → 2-Amino-9-(4-benzoyloxy-3-hydroxymethylbut-1-yl)purine

HRID 5871

Reaktionsgleichung

Reaktionsgleichung von HRID 5871
OCC(C(OC(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)OC)CC[N:6]1[C:14]([NH:15]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[N:13][C:12]2C1=NC(OC)=[N:10][CH:11]=2.[C:60]([O:68][C:69](=O)[C:70]1[CH:75]=[CH:74]C=C[CH:71]=1)(=[O:67])[C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1.C[OH:78].C[N:80]([CH3:83])[CH:81]=O>CN(C)C1C=CN=CC=1>[NH2:15][C:14]1[N:6]=[C:83]2[C:11]([N:10]=[CH:81][N:80]2[CH2:74][CH2:75][CH:70]([CH2:71][OH:78])[CH2:69][O:68][C:60](=[O:67])[C:61]2[CH:62]=[CH:63][CH:64]=[CH:65][CH:66]=2)=[CH:12][N:13]=1

Komponenten

6

Edukt 4

HCID 887MethanolHCID 6228DimethylformamideHCID 7167Benzoic anhydrideHCID 678620909-(3-Hydroxymethyl-4-monomethoxytrityloxybut-1-yl)-2-monomethoxytritylaminopurine

Produkt 1

HCID 138831942-Amino-9-(4-benzoyloxy-3-hydroxymethylbut-1-yl)purine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 142844-(Dimethylamino)pyridineKatalysator

Versuchsvorschrift

To a solution of 9-(3-hydroxymethyl-4-monomethoxytrityloxybut-1-yl)-2-monomethoxytritylaminopurine (0.70 g, 0.9 mmol) and 4-dimethylaminopyridine (10 mg) in N,N-dimethylformamide (5 ml) was added benzoic anhydride (0.61 g, 2.7 mmol) and the solution was stirred for 1 hour. Methanol (1 ml) was added and the solvent was removed. The residue was taken up in 80% acetic acid (9 ml) and the solution was stirred at 80° for 20 minutes. Water (3 ml) was added and the solution was extracted with hexane (2×10 ml). The aqueous layer was retained and the solvent was removed. The residue was partitioned between saturated aqueous sodium bicarbonate and chloroform and the organic layer was dried (magnesium sulphate) and the solvent removed. The residue was purified by column chromatography on silica gel eluting with chloroform-methanol (14:1) to afford 2-amino-9-(4-benzoyloxy-3-hydroxymethylbut-1-yl)purine which was obtained as a white crystalline solid after trituration with methanol (235 mg, 76%), m.p. 116°-118°; λmax (MeOH) 223 (36,700) and 309 (6,680)nm; νmax (KBr) 3320, 1710, 1610, and 1580 cm-1 ; δH [(CD3)2SO]1.83 (1H, m, 3'-H), 1.93 (2H, q, J 7.1 Hz, 2'-H), 3.52 (2H, t, J 5.3 Hz, D2O exchange gives d, CH2OH), 4.19 (2H, t, J 7.0 Hz, 1'-H), 4.2-4.3 (2H, ABX, JAB 11.0 Hz, JAX =JBX 5.6 Hz, CH2OOC), 4.69 (1H, t, J 5.2 Hz, D2O exchangeable, OH), 6.43 (2H, s, D2O exchangeable, 2-NH2), 7.5-7.9 (5H, m, C6H5), 8.10 (1H, s, 8-H), and 8.55 (1H, s, 6-H); (Found: C, 59.20; H, 5.63; N, 20.82%. C17H19N5O3 requires C, 59.81; H, 5.61; N, 20.52%).

Aufarbeitung

  1. customthe solvent was removed
  2. stirringthe solution was stirred at 80° for 20 minutes
  3. additionWater (3 ml) was added
  4. extractionthe solution was extracted with hexane (2×10 ml)
  5. customthe solvent was removed
  6. customThe residue was partitioned between saturated aqueous sodium bicarbonate and chloroform
  7. dry with materialthe organic layer was dried (magnesium sulphate)
  8. customthe solvent removed
  9. customThe residue was purified by column chromatography on silica gel eluting with chloroform-methanol (14:1)

Quellen und Nachweise

ORD-Eintrag
ord-764528aa38624dcfa5184438e1f2dcaa
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05246937

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