Dimethylformamide → HCID 14663383, compound

HRID 268333Notes

Reaction equation

HRID 268333 reaction equation
N#N.C([C:7]1[CH:12]=[CH:11][N:10]=[C:9]([C:13]([NH2:15])=[O:14])[C:8]=1C(N)=O)CCC.[CH2:19]([C:23]1C=CN=C(C(N)=O)C=1C(N)=O)[CH2:20][CH2:21]C.C[N:36](C)[CH:37]=[O:38].C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Pb+4]>O>[CH2:23]([N:15]1[C:13](=[O:14])[C:9]2[N:10]=[CH:11][CH:12]=[CH:7][C:8]=2[NH:36][C:37]1=[O:38])[CH2:19][CH2:20][CH3:21]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 67794569HCID 67794569, compoundHCID 86733186HCID 86733186, compoundHCID 178418268HCID 178418268, compound

Product 1

HCID 14663383HCID 14663383, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 100 ml. flask was charged with 9.0 g. of a mixture of N2 -n-butyl-2,3-pyridine-dicarboxamide and N3 -n-butyl-2,3-pyridine-dicarboxamide suspended in 70 g. dimethylformamide. An 18.0 g. portion of lead tetra-acetate was added, and the reaction mixture stirred at 60° for 2 hours. The reaction mixture was poured into 200 ml. water. The precipitate was filtered from the water, recrystallized from dioxane, and dried at 100°, for about 1 hour. The final yield of 3-n-butyl-pyrido[3,2-d] and 3-n-butyl-pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione amounted to 8.4 g., melting point 200°-210°, and represented 93 percent of theory based on the dicarboxamide starting material. The structure was determined by nuclear magnetic resonance spectroscopy to consist of 78 percent of the [3,2-d]isomer and 22 percent of the [2,3-d]isomer.

Workup

  1. additionflask was charged with 9.0 g
  2. additionThe reaction mixture was poured into 200 ml
  3. filtrationThe precipitate was filtered from the water
  4. customrecrystallized from dioxane
  5. customdried at 100°, for about 1 hour

Sources & evidence

ORD record
ord-aa5b8067a5d44b3397bb25f8b91e2f3d
Source dataset
uspto-grants-1976_03
Patent number
US03947442

Reaction notes

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