2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → Methyl 3-hydroxy-4-oxo-6,7,-dihydro-4h-pyrido[1,2-a]pyrimidine-2-carboxylate

HRID 547379Notes

Reaction equation

HRID 547379 reaction equation
[OH:1][C:2]1[C:7](=[O:8])[N:6]2[CH2:9][CH2:10][CH2:11][CH2:12][C:5]2=[N:4][C:3]=1[C:13]([O:15][CH3:16])=[O:14].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>O1CCOCC1>[OH:1][C:2]1[C:7](=[O:8])[N:6]2[CH2:9][CH2:10][CH:11]=[CH:12][C:5]2=[N:4][C:3]=1[C:13]([O:15][CH3:16])=[O:14]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 59771070methyl 3-hydroxy-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-2-carboxylate

Product 1

HCID 57855395Methyl 3-hydroxy-4-oxo-6,7,-dihydro-4h-pyrido[1,2-a]pyrimidine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of methyl 3-hydroxy-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-2-carboxylate in 1,4,-dioxane was added dichloro-dicyano benzoquinone (1.1 eqs.). The mixture was stirred and heated to 60° C. for 1 hour. TEA (5 eqs.) was added and stirring was continued for 4 hours. The solution was cooled to room temperature and the product was purified by preparative RP-HPLC, using water (0.1% TFA) and acetonitrile (0.1% TFA) as eluants (column: C18). The product was obtained after lyophilization of the pooled product fractions as a fluffy white material.

Workup

  1. additionTEA (5 eqs.) was added
  2. stirringstirring
  3. temperatureThe solution was cooled to room temperature
  4. customthe product was purified by preparative RP-HPLC
  5. customThe product was obtained after lyophilization of the pooled product fractions as a fluffy white material

Sources & evidence

ORD record
ord-bff6fc73542c45af89e71f28f5f2f6c8
Source dataset
uspto-grants-2011_05
Patent number
US07939537B2

Reaction notes

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