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

HRID 1089278Notes

Reaction equation

HRID 1089278 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]([NH:11]C=O)[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[O:14][CH2:15][C@@H:16]1[CH2:20][O:19][C:18]([CH3:22])([CH3:21])[O:17]1.N>CO>[NH2:11][C:9]1[N:8]=[C:7]2[C:3]([N:4]=[CH:5][N:6]2[O:14][CH2:15][C@@H:16]2[CH2:20][O:19][C:18]([CH3:21])([CH3:22])[O:17]2)=[C:2]([Cl:1])[N:10]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 14814208(S)-6-chloro-9-(2,2-dimethyl-1,3-dioxolan-4-ylmethoxy)-2-formamidopurine

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (S)-6-chloro-9-(2,2-dimethyl-1,3-dioxolan-4-ylmethoxy)-2-formamidopurine (400 mg, 1.22 mmol) in methanol (10 ml) and 0.88 ammonia (10 ml) was stirred at 25° C. for 4 h. The solution was evaporated under reduced pressure and the residue chromatographed on silica, eluting with ethyl (2,2-dimethyl-1,3-dioxolan-4-ylmethoxy)purine (270 mg, 74%) as a white Solid; m.p. 118°-120° C. υmax (KBr) 3450, 3320, 3210, 1650, 1630, 1620, 1560, 1510 and 1470 cm-1 ; δH(CDCl3) 1.36(3H,S,CH3), 1.42(3H,S,CH3), 3.85(1H,m,CH2OCMe2), 4.14(1H,m,CH2OCMe2), 4.43(3H,m,CH+CH2ON), 5.51 (2H,br.s,D2O exchangeable, NH2), 8.00(1H,S,H-8). Found: C, 44.45; H, 4.69; N, 23.31%; M+ 299.0795; C11H14ClN5O3 requires C, 44.08; H, 4.71; N, 23.37%; M+ 299.0785.

Workup

  1. customThe solution was evaporated under reduced pressure
  2. customthe residue chromatographed on silica
  3. washeluting with ethyl (2,2-dimethyl-1,3-dioxolan-4-ylmethoxy)purine (270 mg, 74%) as a white Solid

Sources & evidence

ORD record
ord-b0818827f93a49209204761552c0c02c
Source dataset
uspto-grants-1990_10
Patent number
US04965270

Reaction notes

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