Cyanoacetic acid → n-(6-Amino-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-2-cyanoacetamide

HRID 544736Notes

Reaction equation

HRID 544736 reaction equation
O.[NH2:2][C:3]1[C:4](=[O:13])[N:5]([CH3:12])[C:6](=[O:11])[N:7]([CH3:10])[C:8]=1[NH2:9].[C:14]([CH2:16][C:17](O)=[O:18])#[N:15]>>[C:14]([CH2:16][C:17]([NH:2][C:3]1[C:4](=[O:13])[N:5]([CH3:12])[C:6](=[O:11])[N:7]([CH3:10])[C:8]=1[NH2:9])=[O:18])#[N:15]

Participants

3

Reactant 2

HCID 9740Cyanoacetic acidHCID 122574835,6-diamino-1,3-dimethylpyrimidine-2,4(1H,3H)-dione hydrate

Product 1

HCID 225212n-(6-Amino-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-2-cyanoacetamide

Procedure

5,6-Diamino-1,3-dimethyluracil hydrate is reacted with cyanoacetic acid to yield 5-cyanoacetamido-6-amino-1,3-dimethyluracil of the formula: ##STR4## The 5-cyanoacetamido-6-amino-1,3-dimethyluracil is treated with sodium hydroxide within a temperature range of 145°-155° C. to yield 8-carboxymethyltheophylline of the formula: ##STR5## The 8-carboxymethyltheophylline is treated with an alkylated inhibitor of the formula: ##STR6## to yield the compounds of formula (II).

Sources & evidence

ORD record
ord-bf5e700217ec4aa796a4937debfc30b6
Source dataset
uspto-grants-1984_05
Patent number
US04451652

Reaction notes

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