1-Butanol, 4-bromo-, 1-acetate → 4-(2-Anilino-6-chloro-9H-purin-9-yl)butyl acetate

HRID 263941Notes

Reaction equation

HRID 263941 reaction equation
[NH:1]([C:8]1[N:16]=[C:15]2[C:11]([NH:12][CH:13]=[N:14]2)=[C:10]([Cl:17])[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18]([O:21][CH2:22][CH2:23][CH2:24][CH2:25]Br)(=[O:20])[CH3:19]>CN(C=O)C.C(Cl)(Cl)Cl>[NH:1]([C:8]1[N:16]=[C:15]2[C:11]([N:12]=[CH:13][N:14]2[CH2:25][CH2:24][CH2:23][CH2:22][O:21][C:18](=[O:20])[CH3:19])=[C:10]([Cl:17])[N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 784911-Butanol, 4-bromo-, 1-acetateHCID 52718829H-Purin-2-amine, 6-chloro-N-phenyl-

Product 1

HCID 3858914-(2-Anilino-6-chloro-9H-purin-9-yl)butyl acetateYield 45%

Reagents, catalysts & solvents 1

HCID 21754633chloroform N,N-dimethylformamideSolvent

Procedure

Reaction between 2-anilino-6-chloropurine and 4-acetoxybutyl bromide was performed as described in A.a., above, giving 2-anilino-6-chloro-9-(4-acetoxybutyl) purine in a 45% yield (from DMF/chloroform), mp 195°-197° C. 1H NMR δ9.98 (s, 2-NH), 8.32 (s, 8-H), 7.31 (m, C6H5), 4.20 (t, 1'-CH2), 4.02 (t, 4'-CH2), 1.95 (s, CH3), 1.92, 1.58 (m, 2'/3'CH2).

Sources & evidence

ORD record
ord-ac9a61d7a1d2420ebcca417076648ca9
Source dataset
uspto-grants-1997_07
Patent number
US05646155

Reaction notes

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