Sodium Methoxide → HCID 178434373, compound

HRID 894111Notes

Reaction equation

HRID 894111 reaction equation
[CH:1]([NH:3][C:4]1[C:5]([CH3:12])=[N:6][NH:7][C:8]=1[C:9]([NH2:11])=[O:10])=O.C[O-].[Na+]>CN(C)C=O>[OH:10][C:9]1[C:8]2[NH:7][N:6]=[C:5]([CH3:12])[C:4]=2[N:3]=[CH:1][N:11]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 178434625HCID 178434625, compound

Product 1

HCID 178434373HCID 178434373, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-formylamino-3-methylpyrazole-5-carboxamide was cyclized in refluxing dimethylformamide with a catalytic amount of sodium methoxide to produce 7-hydroxy-3-methyl pyrazolo[4,3-d]pyrimidine in about an 80% yield. This reaction is illustrated as follows: ##STR5## Ring closure is thus achieved in this synthetic scheme by an intramolecular mechanism rather than an intermolecular mechanism as is the case in prior processes. This results in a much higher yield of product which is significantly purer than that produced by intermolecular routes.

Sources & evidence

ORD record
ord-5da6a513c5ee4ff39bbed541c3690884
Source dataset
uspto-grants-1981_08
Patent number
US04282361

Reaction notes

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