1,3-Dibromopropane → HCID 20400661, compound

HRID 1980806Notes

Reaction equation

HRID 1980806 reaction equation
O=C1NC(=O)NC2NN=CC1=2.[CH2:12]([N:14]1[C:19]2[N:20]([CH3:23])[N:21]=[CH:22][C:18]=2[C:17](=[O:24])[NH:16][C:15]1=[O:25])[CH3:13].[Br:26][CH2:27][CH2:28][CH2:29]Br>>[Br:26][CH2:27][CH2:28][CH2:29][N:16]1[C:17](=[O:24])[C:18]2[CH:22]=[N:21][N:20]([CH3:23])[C:19]=2[N:14]([CH2:12][CH3:13])[C:15]1=[O:25]

Participants

4

Reactant 3

HCID 80011,3-DibromopropaneHCID 20400669HCID 20400669, compoundHCID 135398752Oxypurinol

Product 1

HCID 20400661HCID 20400661, compound

Procedure

Provided one of the residues R1 or R2 is an alkylcarbonylalkyl group, profitably one can proceed in the way, that the corresponding 4,5,6,7-tetrahydro-4,6-dioxo-pyrazolo-[3,4-d]-pyrimidine is alkylated with a ω-ω'-dibromalkane to ω-alkyl derivative which is treated with acetoaceticester and the reaction product is subjected to a ketone decomposition reaction. For example by such a reaction with the 7-ethyl-4,5,6,7-tetrahydro-1-methyl-4,6-dioxo-1H-pyrazolo-[3,4-d]-pyrimidine with 1,3-dibromopropane, the 5-(3-bromopropyl)-7-ethyl-4,5,6,7-tetrahydro-1-methyl-4,6-dioxo-1H-pyrazolo-[3,4-d]-pyrimidine is obtained, which upon acetoaceticester condensation and subsequent ketone decomposition yields the 7-ethyl-4,5,6,7-tetrahydro-1-methyl-4,6-dioxo-5-(5-oxo-n-hexyl)-1H-pyrazolo-[3,4-d]-pyrimidine. The alkylcarbonyalky rest can also be introduced by direct alkylation reaction of the appropriate 4,5,6,7-tetrahydro-4,6-dioxo-pyrazolopyrimidine, preferably as a sodium salt, with an alkylcarbonylalkylhologenide, preferably a chloride or a bromide. For example a 5-oxo-n-hexyl group can be introduce by using 1-bromohexanone-5.

Workup

  1. customProvided one of the residues
  2. additionis treated with acetoaceticester

Sources & evidence

ORD record
ord-8e76ac558c2f49918a35cb1116ff8c25
Source dataset
uspto-grants-1985_04
Patent number
US04511557

Reaction notes

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