Hydrochloric Acid → 1,3-Propanediol, 2-(2-(2-amino-6-methoxy-9H-purin-9-yl)ethyl)-

HRID 1369997Notes

Reaction equation

HRID 1369997 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][CH2:12][CH:13]2[CH2:18][O:17]C(C)(C)[O:15][CH2:14]2)=[C:4](Cl)[N:3]=1.Cl.[OH2:23].[OH-].[Na+].[CH3:26]O>C[O-].[Na+]>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][CH2:12][CH:13]([CH2:14][OH:15])[CH2:18][OH:17])=[C:4]([O:23][CH3:26])[N:3]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 962WaterHCID 14798Sodium HydroxideHCID 117713466-Chloro-9-[2-(2,2-dimethyl-1,3-dioxan-5-yl)ethyl]-9H-purin-2-amine

Product 1

HCID 5151131,3-Propanediol, 2-(2-(2-amino-6-methoxy-9H-purin-9-yl)ethyl)-Yield 77%

Reagents, catalysts & solvents 1

HCID 10942334Sodium MethoxideSolvent

Procedure

To a solution of 2-amino-6-chloro-9-[2-(2,2-dimethyl-1,3-dioxan-5-yl)ethyl]purine (0.28 g, 0.9 mmol) in methanol (2.5 ml), methanolic sodium methoxide (1M, 1.0 ml) was added and the solution was stirred at 50° for 1.5 hours. The solution was allowed to cool and hydrochloric acid (5M, 0.2 ml) and water (0.4 ml) were added. After 15 minutes the solution was neutralised with 10% aqueous sodium hydroxide. Silica gel was added and the solvent removed. Column chromatography on silica gel eluting with chloroform-methanol mixtures afforded 2-amino-9-(4-hydroxy-3-hydroxymethylbut-1-yl)-6-methoxypurine (185 mg, 77%), m.p. 117-119° C.; λmax (H2O) 213 (ε 22,100), 249 (ε 6,860), and 280 (ε 8,410) nm; νmax (KBr) 3400, 3240, 3210, 1640, 1610, 1590, 1410, and 1395 cm−1; δH [(CD3)2SO] 1.47 (1H, m, CHCH2CH2), 1.74 (2H, q, J 7 Hz, CHCH2CH2), 3.40 (4H, d, J 6 Hz, 2×CH2O), 3.95 (3H, s, OCH3), 4.06 (2H, t, J 7 Hz, CH2N), 4.4 (2H, br, D2O exchangeable, 2×OH), 6.33 (2H, s, D2O exchangeable, 2-NH2), and 7.46 (1H, s, 8-H) (Found: M+ 267.1340; C11H17N5O3 requires M+ 267.1331).

Workup

  1. temperatureto cool
  2. additionSilica gel was added
  3. customthe solvent removed

Sources & evidence

ORD record
ord-8adc8f71622c41d5b76d63461e1fef17
Source dataset
uspto-grants-2003_06
Patent number
US06579981B1

Reaction notes

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