(S)-2-Amino-6-chloro-9-(2,2-dimethyl-1,3-dioxolan-4-ylmethoxy)purine → (S)-2-Amino-6-chloro-9-(2,3-dihydroxyprop-1-oxy)purine

HRID 1089279Notes

Reaction equation

HRID 1089279 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[O:11][CH2:12][C@@H:13]2[CH2:17][O:16]C(C)(C)[O:14]2)=[C:4]([Cl:20])[N:3]=1>C(O)(=O)C>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[O:11][CH2:12][C@@H:13]([OH:14])[CH2:17][OH:16])=[C:4]([Cl:20])[N:3]=1

Participants

3

Reactant 1

HCID 14814211(S)-2-Amino-6-chloro-9-(2,2-dimethyl-1,3-dioxolan-4-ylmethoxy)purine

Product 1

HCID 14814189(S)-2-Amino-6-chloro-9-(2,3-dihydroxyprop-1-oxy)purine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of (S)-2-amino-6-chloro-9-(2,2-dimethyl-1,3-dioxolan-4-ylmethoxy)purine (250 mg, 0.83 mmol) in 80% acetic acid (20 ml) was stirred at 25° C. for 2 h. and then at 70° C. for 1 h. The solution was evaporated to dryness under reduced pressure, the residue absorbed on silica and chromatographed eluting with acetone-hexane 3:1 affording (S)-2-amino-6-chloro-9-(2,3-dihydroxyprop-1-oxy)purine (170 mg, 78%) as a white solid; m.p. 155°-8° C. υmax (KBr) 3340, 3200, 1660, 1620, 1560, 1520 1470 cm-1 ; δH[(CD3)2SO] 3.41(2H,m,CH2OH) 3.78(1H,m,CH), 4.19(1H,q,J7.4,10.4 Hz,CH2ON), 4.40(1H,q,J3.3,10.4 Hz,CH2ON), 4.73(1H,t,J5.0 Hz,D2O exchangeable, OH), 5.14(1H,d,J5.0 Hz.D2O exchangeable, OH), 7.12(2H,S,D2O exchangeable, NH2) 8.35(1H,S,H-8). Found M+ 259.0475; C8H10ClN5O3 requires M+ 259.0472.

Workup

  1. customThe solution was evaporated to dryness under reduced pressure
  2. customthe residue absorbed on silica
  3. customchromatographed
  4. washeluting with acetone-hexane 3:1 affording (S)-2-amino-6-chloro-9-(2,3-dihydroxyprop-1-oxy)purine (170 mg, 78%) as a white solid

Sources & evidence

ORD record
ord-26007b199d534aa9839a44f2ea5e4a67
Source dataset
uspto-grants-1990_10
Patent number
US04965270

Reaction notes

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