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

HRID 971212
Notes
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Reaction equation

HRID 971212 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.CCN(C(C)C)C(C)C.Cl[C:22]1[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][N:23]=1>O1CCOCC1.CC(N(C)C)=O>[Cl:28][C:27]1[C:22]([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:23][CH:24]=[CH:25][CH:26]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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)-one

Reagents, catalysts & solvents 1

HCID 67000103dioxane N,N-dimethylacetamideSolvent

Conditions

Temperature
150 °C

Procedure

5,6,7,8-Tetrahydro-3H-pyrido[3,4-d]pyrimidin-4-one (1.5 g, 10 mmol) was dissolved in a mixture of dioxane-dimethylacetamide (2 ml, 3:1) and 2,3-dichloropyridine was added (1.5 g, 10 mmol), followed by DIEA (1.7 ml; 10 mmol). The mixture was heated at 150° C. for 2 hours in a microwave (Personal Chemistry, Smith Creator). The solvents were evaporated and the residue was dissolved in a 3:1 mixture of chloroform-isopropanol and washed with water. The organic layer washed with brine, dried over soldium sulphate, filtered and evaporated to give a yellow solid (3 g). The crude material was used for the subsequent step.

Workup

  1. additionwas added (1.5 g, 10 mmol)
  2. customThe solvents were evaporated
  3. dissolutionthe residue was dissolved in a 3:1 mixture of chloroform-isopropanol
  4. washwashed with water
  5. washThe organic layer washed with brine
  6. customdried
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-eee96b2cffb14e46afb2a4322d035885
Source dataset
uspto-grants-2007_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07312330B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes