Hydrochloric Acid → 7-(2-Hydroxyethyl)adenine

HRID 2417230Notes

Reaction equation

HRID 2417230 reaction equation
C[O:2][C:3]([CH2:5][N:6]1[C:14]2[C:9](=[N:10][CH:11]=[N:12][C:13]=2[NH2:15])[N:8]=[CH:7]1)=O.O.[BH4-].[Na+].Cl>C1COCC1>[OH:2][CH2:3][CH2:5][N:6]1[C:14]2[C:9](=[N:10][CH:11]=[N:12][C:13]=2[NH2:15])[N:8]=[CH:7]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 11127467HCID 11127467, compound

Product 1

HCID 110194367-(2-Hydroxyethyl)adenineYield 55.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a stirred solution containing 16 (0.207 g, 0.999 mmol) and water (0.50 mL) in THF (12 mL) was added NaBH4 (0.38 g, 10.0 mmol). After stirring for 4 h at 25° C., the reaction mixture was neutralized to pH=7.0 by use of 10% HCl aqueous solution. Solvent was evaporated under reduced pressure and the residue was purified by column chromatography (EtOAc/hexanes=9:1) to give 18 (0.10 g, 0.55 mmol) in 55% yield: mp 132-133° C.; Rf(hexanes/EtOAc=1:2) 0.09; UV (EtOH) λmax 265 (ε 14,110); 1H NMR (CD3OD) δ 3.68 (t, J=5.9 Hz, 2 H, CH2O), 3.66 (t, J=5.9 Hz, 2 H, CH2N), 8.34 (s, 1 H, HC2), 8.68 (s, 1 H, HC8); MS m/z 179 (M+). Anal (C7H9N5O) C, H, N; calcd (%): 46.92, 5.06, 39.08; found (%): 47.01, 5.12, 39.11.

Workup

  1. customSolvent was evaporated under reduced pressure
  2. customthe residue was purified by column chromatography (EtOAc/hexanes=9:1)

Sources & evidence

ORD record
ord-ea0fffcb3411499e90a6d51fed39e29f
Source dataset
uspto-grants-2004_11
Patent number
US06825348B2

Reaction notes

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