2-(Chloromethoxy)ethyl benzoate → 2,6-Dichloro-9-(2-benzoyloxyethoxymethyl)purine

HRID 614923Notes

Reaction equation

HRID 614923 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([Cl:11])[N:3]=1.[C:12]([O:20][CH2:21][CH2:22][O:23][CH2:24]Cl)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:24][O:23][CH2:22][CH2:21][O:20][C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:4]([Cl:11])[N:3]=1

Participants

3

Reactant 2

HCID 27245002-(Chloromethoxy)ethyl benzoateHCID 53244122,6-Dichloropurine

Product 1

HCID 128995852,6-Dichloro-9-(2-benzoyloxyethoxymethyl)purineYield 41%

Procedure

Following the procedure of Example 1, 2,6-dichloropurine was condensed with 1-benzoyloxy-2-chloromethoxyethane to give a 41% yield of 2,6-dichloro-9-(2-benzoyloxyethoxymethyl)purine, m.p. 121°-125° C. This was treated according to the procedure of Example 2 to give simultaneous ammonolysis of the 6-chloro and benzoyloxy groups yielding 2-chloro-9-(hydroxyethoxymethyl)adenine, in 94% yield, m.p. 188°-190° C. after recrystallization from isopropanol.

Sources & evidence

ORD record
ord-0d5f14841cac4f93873dac47df360068
Source dataset
uspto-grants-1979_03
Patent number
US04146715

Reaction notes

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