2,3-Dichloropyridine → 7-(3-Chloropyridin-2-yl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4(3H)-one

HRID 2219969Notes

Reaction equation

HRID 2219969 reaction equation
[N:1]1[C:6]2[CH2:7][NH:8][CH2:9][CH2:10][C:5]=2[C:4](=[O:11])[NH:3][CH:2]=1.Cl[C:13]1[C:18]([Cl:19])=[CH:17][CH:16]=[CH:15][N:14]=1.C(N(CC)C(C)C)(C)C>O1CCOCC1.CN(C)C(=O)C>[Cl:19][C:18]1[C:13]([N:8]2[CH2:9][CH2:10][C:5]3[C:4](=[O:11])[NH:3][CH:2]=[N:1][C:6]=3[CH2:7]2)=[N:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 169882,3-DichloropyridineHCID 81531DiisopropylethylamineHCID 1357416015,6,7,8-Tetrahydropyrido[3,4-D]pyrimidin-4(3H)-one

Product 1

HCID 1359974627-(3-Chloropyridin-2-yl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4(3H)-oneYield 86%

Reagents, catalysts & solvents 1

HCID 67000103dioxane N,N-dimethylacetamideSolvent

Conditions

Temperature
150 °C

Procedure

5,6,7,8-Tetrahydropyrido[3,4-d]pyrimidin-4(3H)-one (600 mg, 4.0 mmol) was dissoled in a mixture of dioxane/N,N-dimethylacetamide (4:1) (2 mL). To the mixture was added 2,3-dichloropyridine (1.8 g, 12.0 mmol) and N,N-diisopropylethylamine (0.7 mL, 4.0 mmol). The mixture was heated at 150° C. in a microwave (Emrys Optimizer model, Personal Chemistry) for 16 h. The solvents were removed under vacuum and the residue was dissolved in ethyl acetate and washed with sat. NaHCO3 and brine. The organic layer was dried over Na2SO4, filtered and evaporated to give a yellow solid (900 mg, 86%), which was used as such for the next step.

Workup

  1. customThe solvents were removed under vacuum
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with sat. NaHCO3 and brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-7f834324540f42c9a8fc7dd93371a92b
Source dataset
uspto-grants-2008_08
Patent number
US07414131B2

Reaction notes

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