HCID 178434627, compound → HCID 178434626, compound

HRID 894120Notes

Reaction equation

HRID 894120 reaction equation
[CH3:1][C:2]1[C:6]([N+:7]([O-:9])=[O:8])=[C:5]([C:10]([OH:12])=O)[NH:4][N:3]=1.[CH3:13][C:14]1[C:18]([N+:19]([O-:21])=[O:20])=[C:17]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[NH:16][N:15]=1>>[CH3:1][C:2]1[C:6]([N+:7]([O-:9])=[O:8])=[C:5]([C:10]([NH2:15])=[O:12])[NH:4][N:3]=1.[CH3:13][C:14]1[C:18]([N+:19]([O-:21])=[O:20])=[C:17]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[NH:16][N:15]=1

Participants

4

Reactant 2

HCID 178434627HCID 178434627, compoundHCID 178470423HCID 178470423, compound

Product 2

HCID 178434626HCID 178434626, compoundHCID 178470423HCID 178470423, compound

Procedure

In a method for synthesizing 7-alkylamino-3-methylpyrazolo[4,3-d]pyrimidines, including the steps of esterifying 3-methyl-4-nitropyrazole-5-carboxylic acid to ethyl 3-methyl-4-nitropyrazole-5-carboxylate, forming 3-methyl-4-nitropyrazole-5-carboxamide from ethyl 3-methyl-4-nitropyrazole-5-carboxylate, catalytically reducing and formylating ethyl 3-methyl-4-nitropyrazole-5-carboxamide to produce 4-formylamino-3-methylpyrazole-5-carboxamide, closing the ring of 4-formylamino-3-methylpyrazole-5-carboxamide to produce 3-methyl-7-hydroxypyrazolo[4,3-d]pyrimidine, chlorinating said 3-methyl-7-hydroxypyrazolo [4,3-d]pyrimidine to produce 7-chloro-3-methylpyrazolo-[4,3-d], and reacting said 7-chloro-3-methylpyrazolo[4,3-d]pyrimidine with an alkylamine to produce a 7-alkylamino-3-methylpyrazolo[4,3-d]pyrimidine:

Sources & evidence

ORD record
ord-b815209ddc444b1691310bfda21e1f33
Source dataset
uspto-grants-1981_08
Patent number
US04282361

Reaction notes

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