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

HRID 1461515Notes

Reaction equation

HRID 1461515 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 (1 M, 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 (5 M, 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 (ε22,100), 249 (ε6,860), and 280 (ε8,410) nm; νmax (KBr) 3400, 3240, 3210, 1640, 1610, 1590, 1410, and 1395 cm-1 ; δ H [(CD3)2SO] 1.47 (1 H, m, CHCH2CH2), 1.74 (2 H, q, J 7 Hz, CHCH2CH2), 3.40 (4 H, d, J 6 Hz, 2×CH2O), 3.95 (3 H, s, OCH3), 4.06 (2 H, t, J 7 Hz, CH2N), 4.4 (2 H, br, D2O exchangeable, 2×OH), 6.33 (2 H, s, D2O exchangeable, 2-NH2), and 7.46 (1 H, 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-5c6c57643e1c42ce8e9afccb63395934
Source dataset
uspto-grants-1991_12
Patent number
US05075445

Reaction notes

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