Benzyl Alcohol → HCID 13869778, compound

HRID 1369999Notes

Reaction equation

HRID 1369999 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.[Na].Cl.O.[CH2:25]([OH:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>>[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:32][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:3]=1

Participants

6

Reactant 5

HCID 244Benzyl AlcoholHCID 313Hydrochloric AcidHCID 962WaterHCID 5360545SodiumHCID 117713466-Chloro-9-[2-(2,2-dimethyl-1,3-dioxan-5-yl)ethyl]-9H-purin-2-amine

Product 1

HCID 13869778HCID 13869778, compoundYield 50%

Procedure

A suspension of 2-amino-6-chloro-9-[2-(2,2-dimethyl-1,3-dioxan-5-yl)ethyl]purine (0.31 g, 1.0 mmol) in a solution of sodium benzoxide (1M in benzyl alcohol, 2 ml) was stirred at 70° for 1 hour. The resulting solution was allowed to cool, hydrochloric acid (5M, 0.4 ml) and water (0.6 ml) were added and the solution was stirred for 1 hour at room temperature. The solution was then partitioned between chloroform and water. The aqueous layer was neutralised with aqueous sodium bicarbonate and extracted with chloroform. The combined organic layers were washed with aqueous sodium bicarbonate, dried (magnesium sulphate) and the solvent was removed. The residue was purified by column chromatography on silica gel eluting with chloroform-methanol mixtures (10:1, 5:1) to afford 2-amino-6-benzyloxy-9-(4-hydroxy-3-hydroxymethylbut-1-yl)purine as a white crystalline solid (0.17 g, 50%), m.p. 146-147.5° C.; λmax (EtOH) 212 (32,300), 250 (8,380), and 283 (10,100) nm; νmax (KBr) 3340, 3220, 1655, 1605, and 1580 cm−1; δH [(CD3)2SO] 1.3-1.6 (1H, m, 3′-H), 1.72 (2H, q, J 7 Hz, 2′-H), 3.38 (4H, AB part of ABX, 2×4′-H), 4.03 (2H, t, J 7 Hz, 1′-H), 4.36 (2H, t, J 5.5 Hz, D2O exchangeable, 2×OH), 5.47 (2H, s, PhCH2), 6.37 (2H, s, D2O exchangeable, 2-NH2), 7.3-7.6 (5H, m, C6H5), and 7.84 (1H, s, 8-H); (Found: C, 58.89; H, 6.12; N, 19.87%; C17H21N5O3 requires C, 59.46; H, 6.16; N, 20.40%).

Workup

  1. temperatureto cool
  2. stirringthe solution was stirred for 1 hour at room temperature
  3. customThe solution was then partitioned between chloroform and water
  4. extractionextracted with chloroform
  5. washThe combined organic layers were washed with aqueous sodium bicarbonate
  6. dry with materialdried (magnesium sulphate)
  7. customthe solvent was removed
  8. customThe residue was purified by column chromatography on silica gel eluting with chloroform-methanol mixtures (10:1, 5:1)

Sources & evidence

ORD record
ord-ef5573986a284fa0ad1ce76c14cece12
Source dataset
uspto-grants-2003_06
Patent number
US06579981B1

Reaction notes

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