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

HRID 1532083
Notes
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Reaction equation

HRID 1532083 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
ParticipantsProcedureSources & evidenceReaction notes

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 962Water
Solvent

Procedure

A solution of the crude product of Example 42 (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-6d1ae687d1af44bfa1792c5d973fae33
Source dataset
uspto-grants-2001_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06200980B1

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes