2H-pyran-3,5(4H,6H)-dione → methyl 4-(3-iodo-4-methylphenyl)-2-methyl-5-oxo-4,5,6,8-tetrahydro-1H-pyrano[3,4-b]pyridine-3-carboxylate

HRID 987385Notes

Reaction equation

HRID 987385 reaction equation
[O:1]1[CH2:6][C:5](=O)[CH2:4][C:3](=[O:8])[CH2:2]1.[I:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[CH3:18])[CH:13]=O.[NH2:19]/[C:20](/[CH3:26])=[CH:21]\[C:22]([O:24][CH3:25])=[O:23]>CO>[I:9][C:10]1[CH:11]=[C:12]([CH:13]2[C:21]([C:22]([O:24][CH3:25])=[O:23])=[C:20]([CH3:26])[NH:19][C:5]3[CH2:6][O:1][CH2:2][C:3](=[O:8])[C:4]2=3)[CH:15]=[CH:16][C:17]=1[CH3:18]

Participants

5

Reactant 3

HCID 3252872H-pyran-3,5(4H,6H)-dioneHCID 643918Methyl 3-aminocrotonateHCID 123302543-Iodo-4-methylbenzaldehyde

Product 1

HCID 18001003methyl 4-(3-iodo-4-methylphenyl)-2-methyl-5-oxo-4,5,6,8-tetrahydro-1H-pyrano[3,4-b]pyridine-3-carboxylateYield 45.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The product from Example 1C (0.34 g, 3.0 mmol), the product from Example 3A (0.74 g, 3.0 mmol) and methyl 3-aminocrotonate (0.35 g, 3.0 mmol) in methanol (8 mL) were heated to 80° C. in a sealed tube for 60 hours. After cooling to ambient temperature, the mixture was filtered and the filter cake washed with methanol and dried to provide the title compound (0.60 g).

Workup

  1. filtrationthe mixture was filtered
  2. washthe filter cake washed with methanol
  3. customdried

Sources & evidence

ORD record
ord-42be9a9624214975863e00402913c28e
Source dataset
uspto-grants-2003_10
Patent number
US06632418B2

Reaction notes

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