6-Chloro-9-[2-(2,2-dimethyl-1,3-dioxan-5-yl)ethyl]-9H-purin-2-amine → 2-Amino-6-chloro-9-(4-hydroxy-3-hydroxymethylbut-1-yl)purine hydrochloride

HRID 1368681Notes

Reaction equation

HRID 1368681 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:21])[N:3]=1>O1CCCC1.Cl>[ClH:21].[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]([CH2:18][OH:17])[CH2:14][OH:15])=[C:4]([Cl:21])[N:3]=1

Participants

4

Reactant 1

HCID 117713466-Chloro-9-[2-(2,2-dimethyl-1,3-dioxan-5-yl)ethyl]-9H-purin-2-amine

Product 1

HCID 138697722-Amino-6-chloro-9-(4-hydroxy-3-hydroxymethylbut-1-yl)purine hydrochlorideYield 125.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-amino-6-chloro-9-[2-(2,2-dimethyl-1,3-dioxan-5-yl)ethyl]purine (0.46 g, 1.5 mmol) in tetrahydrofuran (4.5 ml), hydrochloric acid (2.0M, 0.5 ml) was added. A white precipitate formed and after 0.5 hour the solution was diluted with further tetrahydrofuran and was filtered to give 2-amino-6-chloro-9-(4-hydroxy-3-hydroxymethylbut-1-yl)purine hydrochloride (290 mg, 63%), decomposed over 165° C.; λmax (H2O, pH5.5) 223 (ε 28,400), 245 (ε 4,620), and 307 (ε 7,620) nm; νmax (KBr) 3370, 3330, 3200, 2500, 1650, 1630, 1595, and 1505 cm−1; δH [(CD3)2SO] 1.53 (1H, m, CHCH2CH2), 1.83 (2H, q, J 7 Hz, CHCH2CH2), 3.35 (4H, d, J 6 Hz, 2×CH2O), 4.19 (2H, t, J 7 Hz, CH2N), 5.85 (9H, s, D2O exchangeable, 2×OH, NH2, HCl and H2O), and 8.57 (1H, s, 8-H). (Found: C, 39.04; H, 4.85; N, 22.36%; C10H14ClN5O4.HCl requires C, 38.98; H, 4.91; N, 22.73.%).

Workup

  1. customA white precipitate formed and after 0.5 hour the solution
  2. filtrationwas filtered

Sources & evidence

ORD record
ord-33ec683bc5b7473e9cda636c3d4e741a
Source dataset
uspto-grants-2003_06
Patent number
US06573378B1

Reaction notes

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