Acetic Acid → 2-(5-Amino-2-propoxyphenyl)-purin-6-one

HRID 1460973Notes

Reaction equation

HRID 1460973 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][C:6]=1[C:14]1[N:22]=[C:21]2[C:17](=[N:18][CH:19]=[N:20]2)[C:16](=[O:23])[N:15]=1)[CH2:2][CH3:3].[OH-].[Na+].C(O)(=O)C>O.[Pd]>[NH2:11][C:8]1[CH:9]=[CH:10][C:5]([O:4][CH2:1][CH2:2][CH3:3])=[C:6]([C:14]2[N:22]=[C:21]3[C:17](=[N:18][CH:19]=[N:20]3)[C:16](=[O:23])[N:15]=2)[CH:7]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 212508282-(2-Propoxy-5-nitrophenyl)purin-6-one

Product 1

HCID 212506802-(5-Amino-2-propoxyphenyl)-purin-6-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A solution of the crude product of Example 11 (1.5 g) in water (50 ml) containing 2 Normal sodium hydroxide (2.3 ml) and 10% palladium on charcoal (0.15 g) was shaken under hydrogen (50 psi) until the uptake was complete. Neutralisation of the filtered solution with acetic acid gave a fine precipitate of 2-(5-amino-2-propoxyphenyl)-purin-6-one. This mixture was warmed with 2 Normal hydrochloric acid (2.5 ml) and the solution was treated with acetic anhydride (0.55 ml) and sodium acetate trihydrate (0.8 g). The mixture was warmed for 10 minutes then cooled and filtered to give a crude product (1.02 g) which was recrystallised from aqueous dimethylformamide twice to give the title compound, 0.49 g, m.p. 320°-323° C.

Sources & evidence

ORD record
ord-ab969f80b8f04a7382b2e1b53d882352
Source dataset
uspto-grants-1991_12
Patent number
US05073559

Reaction notes

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