Phenylhydrazine → Methyl 6-[3,5-dimethyl-1-phenyl-1H-pyrazol-4-ylmethyl]-1-isobutyl-3-methyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-5-carboxylate

HRID 131578Notes

Reaction equation

HRID 131578 reaction equation
Br[CH2:2][C:3]1[S:18][C:6]2[N:7]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:8](=[O:13])[N:9]([CH3:12])[C:10](=[O:11])[C:5]=2[C:4]=1[C:19]([O:21][CH3:22])=[O:20].[C:23]1([NH:29][NH2:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C/C(/O)=C/C(C)=O.C/C(/O)=C/C(C)=O.[Zn]>[CH3:2][C:3]1[C:4]([CH2:2][C:3]2[S:18][C:6]3[N:7]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:8](=[O:13])[N:9]([CH3:12])[C:10](=[O:11])[C:5]=3[C:4]=2[C:19]([O:21][CH3:22])=[O:20])=[C:5]([CH3:6])[N:29]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:30]=1

Participants

4

Reactant 2

HCID 7516PhenylhydrazineHCID 16102871Methyl 6-bromomethyl-1-isobutyl-3-methyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-5-carboxylate

Product 1

HCID 68805830Methyl 6-[3,5-dimethyl-1-phenyl-1H-pyrazol-4-ylmethyl]-1-isobutyl-3-methyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-5-carboxylate

Reagents, catalysts & solvents 1

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

Procedure

Prepared from methyl 6-(bromomethyl)-1-isobutyl-3-methyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-5-carboxylate (500 mg), zinc acetylacetonate hydrate and phenyl hydrazine following the procedure of example 26, part a). Crude product was purified by column chromatography over silica, eluting with ethyl acetate/iso-hexane (2:3) to give the sub-title compound (555 mg) as a solid. MS(ESI) 481 [M+H]+. δ 1HDMSO 0.95 (6H, d), 2.24 (3H, s), 2.27 (3H, s), 2.20-2.30 (1H, m), 3.39 (3H, s), 3.71 (2H, d), 3.95 (3H, s), 3.96 (2H, s), 7.36-7.50 (5H, m).

Workup

  1. customCrude product was purified by column chromatography over silica
  2. washeluting with ethyl acetate/iso-hexane (2:3)

Sources & evidence

ORD record
ord-848c614b30594808b54c84a66eacb594
Source dataset
uspto-grants-2008_06
Patent number
US07384950B2

Reaction notes

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