Pyridine → 97845-82-4

HRID 1368689Notes

Reaction equation

HRID 1368689 reaction equation
CO[N:3](C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:4]1[NH:5][C:6](=[O:41])[C:7]2[N:8]=[CH:9][N:10]([CH:13](OC(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH2:14][CH:15]([CH2:19][OH:20])[CH2:16][O:17][CH3:18])[C:11]=2[N:12]=1.C(Cl)(=[O:67])CCCCC.N1[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=1>>[C:18]([O:17][CH2:16][CH:15]([CH2:19][OH:20])[CH2:14][CH2:13][N:10]1[CH:9]=[N:8][C:7]2[C:6](=[O:41])[NH:5][C:4]([NH2:3])=[N:12][C:11]1=2)(=[O:67])[CH2:70][CH2:71][CH2:72][CH2:73][CH3:74]

Participants

4

Reactant 3

HCID 1049PyridineHCID 67340Hexanoyl chlorideHCID 136341217HCID 136341217, compound

Product 1

HCID 13548073597845-82-4Yield 38%

Procedure

To a solution of N2-monomethoxytrityl-9-(4-monomethoxy-trityloxy3-hydroxymethylbut-1-yl)guanine (0.72 g, 0.9 mmol) in pyridine (4 ml) was added hexanoyl chloride (0.38 ml, 2.7 mmol) and the solution was stirred for 20 minutes. The mixture was precipitated in water (40 ml) and the resulting precipitate was stirred in 80% acetic acid (10 ml) at 80° for 45 minutes. The solvent was removed and the residue purified by column chromatography on silica gel eluting with chloroform-methanol mixtures (7:1, 5:1) to afford 9-(4-hexanoyloxy-3-hydroxymethylbut-1-yl)guanine (0.12 g, 38%), m.p. 179-181° C.; νmax 2960, 2930, 1730, 1690, 1630, and 1600 cm−1; δH [(CD3)2SO] 0.84 (3H, t, J 6.9 Hz, CH3), 1.24 (4H, m, CH3(CH2)2), 1.50 (2H, quintet, J 7.3 Hz, CH2CH2CO), 1.6-1.8 (3H, m, 2′-H and 3′-H), 2.26 (2H, t, J 7.3 Hz, CH2CO), 3.40 (2H, t, J 5 Hz, D2O exchange leaves d, CH2OH), 3.9-4.1 (4H, m, 1′-H and CH2OCO), 4.60 (1H, t, J 5.1 Hz, D2O exchangeable, 2-NH2), 7.67 (1H, s, 8-H), and 10.49 (1H, s, D2O exchangeable, 1-H); (Found: C, 52.63; H, 6.91; N, 18.75:%; C16H25N5O4 requires: C, 54.69; H, 7.17; N, 19.93%).

Workup

  1. customThe mixture was precipitated in water (40 ml)
  2. stirringthe resulting precipitate was stirred in 80% acetic acid (10 ml) at 80° for 45 minutes
  3. customThe solvent was removed
  4. customthe residue purified by column chromatography on silica gel eluting with chloroform-methanol mixtures (7:1, 5:1)

Sources & evidence

ORD record
ord-93b60fb2c4224905b784e69bd773b519
Source dataset
uspto-grants-2003_06
Patent number
US06573378B1

Reaction notes

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