Formic Acid → 6H-Purin-6-one, 2-amino-9-(4-(formyloxy)-3-((formyloxy)methyl)butyl)-1,9-dihydro-

HRID 1461521Notes

Reaction equation

HRID 1461521 reaction equation
[OH:1][CH2:2][CH:3]([CH2:17][OH:18])[CH2:4][CH2:5][N:6]1[CH:14]=[N:13][C:12]2[C:11](=[O:15])[NH:10][C:9]([NH2:16])=[N:8][C:7]1=2.C1(N=C=NC2CCCCC2)CCCCC1.[CH:34]([OH:36])=O.CN(C)[CH:39]=[O:40]>CN(C)C1C=CN=CC=1>[CH:39]([O:1][CH2:2][CH:3]([CH2:17][O:18][CH:34]=[O:36])[CH2:4][CH2:5][N:6]1[CH:14]=[N:13][C:12]2[C:11](=[O:15])[NH:10][C:9]([NH2:16])=[N:8][C:7]1=2)=[O:40]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 6228DimethylformamideHCID 10868DicyclohexylcarbodiimideHCID 135398748Penciclovir

Product 1

HCID 1354807336H-Purin-6-one, 2-amino-9-(4-(formyloxy)-3-((formyloxy)methyl)butyl)-1,9-dihydro-

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

A mixture of 9-(4-hydroxy-3-hydroxymethylbut-1-yl)-guanine (0.23 g, 0.9 mmol), dicyclohexylcarbodiimide (0.92 g, 4.5 mmol), formic acid (0.17 ml, 4.5 mmol), 4-dimethylaminopyridine (20 mg) and N,N-dimethylformamide (5 ml) was stirred for 40 minutes at room temperature and then quenched by addition of methanol (1 ml). The solution was filtered and the solvent removed. The residue was purified by column chromatography on silica gel eluting with chloroformethanol mixtures (7:1, 4:1) to afford 9-(4-formyloxy-3-formyloxymethylbut-1-yl)guanine which was crystallised from methanol (0.12 g, 43%), m.p. 195°-198° C.; νmax (KBr) 1720, 1680, 1630, 1600, and 1570 cm-1 ; δH [(CD3)2SO] 1.83 (2 H, q, J 7.1 Hz, 2'-H), 2.01 (1 H, m, 3'-H), 4.04 (2 H, t, J 7.1 Hz, 1'-H), 4.13 (4 H, d, J 5.5 Hz, 2×4'-H), 6.39 (2 H, s, D2O exchangeable, 2-NH2), 7.70 (1 H, s, 8-H), 8.23 (2 H, s, 2×HCOO), and 10.52 (1 H, s, D2O exchangeable, 1-H); (Found: C, 45.40; H, 4.68; N, 21.70%; C12H15N5O5 requires: C, 46.60; H, 4.89; N, 22.64%).

Workup

  1. customquenched by addition of methanol (1 ml)
  2. filtrationThe solution was filtered
  3. customthe solvent removed
  4. customThe residue was purified by column chromatography on silica gel eluting with chloroformethanol mixtures (7:1, 4:1)

Sources & evidence

ORD record
ord-909c2516df2141789ba3ee3be9c1154c
Source dataset
uspto-grants-1991_12
Patent number
US05075445

Reaction notes

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