2-Hydrazinopyridine → [3,5-Dimethyl-1-(2-pyridyl)-1H-pyrazol-4-yl]methyl-1,2,3,4-tetrahydro-3-methyl-1-(1-methylethyl)-2,4-dioxothieno[2,3-d]pyrimidine-5-carboxylic acid methyl ester

HRID 131627Notes

Reaction equation

HRID 131627 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:13]2[C:12](=[O:14])[N:11]([CH3:15])[C:10](=[O:16])[N:9]([CH:17]([CH3:19])[CH3:18])[C:8]=2[S:7][C:6]=1[CH2:20]Br)=[O:4].[NH:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1)[NH2:23]>C/C(/O)=C/C(C)=O.C/C(/O)=C/C(C)=O.[Zn]>[CH3:1][O:2][C:3]([C:5]1[C:13]2[C:12](=[O:14])[N:11]([CH3:15])[C:10](=[O:16])[N:9]([CH:17]([CH3:19])[CH3:18])[C:8]=2[S:7][C:6]=1[CH2:20][C:5]1[C:6]([CH3:20])=[N:23][N:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=2)[C:13]=1[CH3:8])=[O:4]

Participants

4

Reactant 2

HCID 786452-HydrazinopyridineHCID 68806593Methyl 6-(bromomethyl)-1-isopropyl-3-methyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-5-carboxylate

Product 1

HCID 86603576[3,5-Dimethyl-1-(2-pyridyl)-1H-pyrazol-4-yl]methyl-1,2,3,4-tetrahydro-3-methyl-1-(1-methylethyl)-2,4-dioxothieno[2,3-d]pyrimidine-5-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 10912358Bis(pentane-2,4-dionato-O,O')zincCatalyst

Procedure

Prepared from 6-(bromomethyl)-1,2,3,4-tetrahydro-3-methyl-1-(1-methylethyl)-2,4-dioxothieno[2,3-d]pyrimidine-5-carboxylic acid methyl ester, zinc acetylacetonate hydrate and 2-hydrazinopyridine by the method of example 1 part e) to give the sub-title compound.

Sources & evidence

ORD record
ord-ce3fe980149d4162928905f5ebc01ebb
Source dataset
uspto-grants-2008_06
Patent number
US07384951B2

Reaction notes

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