Acetone Cyanohydrin → HCID 67065613, compound

HRID 1846408Notes

Reaction equation

HRID 1846408 reaction equation
[CH:1]1([N:7]2[C:12](=[O:13])[C:11]([C:14](O)=[O:15])=[CH:10][N:9]=[C:8]2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(Cl)(=O)C(Cl)=O.[C:29]1(=[O:36])[CH2:34][CH2:33][CH2:32][C:31](=[O:35])[CH2:30]1.C(N(CC)CC)C.OC(C)(C)C#N>ClCCl.CN(C)C=O>[CH:1]1([N:7]2[C:12](=[O:13])[C:11]([C:14]([CH:30]3[C:31](=[O:35])[CH2:32][CH2:33][CH2:34][C:29]3=[O:36])=[O:15])=[CH:10][N:9]=[C:8]2[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

8

Reactant 5

HCID 6406Acetone CyanohydrinHCID 8471Triethylamine2×HCID 104341,3-CyclohexanedioneHCID 65578Oxalyl chlorideHCID 67954869HCID 67954869, compound2×

Product 1

HCID 67065613HCID 67065613, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To 1-cyclohexyl-1,6-dihydro-6-oxo-2-phenyl-5-pyrimidinecarboxylic acid (i.e. the product from Example 11, Step B) (0.58 g, 1.5 mmol) in 10 mL of dichloromethane was added oxalyl chloride (0.490 g, 3.9 mmol) and one drop of N,N-dimethylformamide. The reaction was stirred at ambient temperature for 2 h and then concentrated under reduced pressure. The crude oil was then redissolved in 10 mL of dichloromethane and then treated with 1,3-cyclohexanedione (0.24 g, 2.1 mmol) and triethylamine (0.39 g, 3.8 mmol) stirred for 30 min, then treated with a catalytic amount of 2-hydroxy-2-methyl-propanenitrile (0.015 g, 0.15 mmol) and triethylamine (0.393 g, 3.8 mmol) and stirred at ambient temperature for 16 h. The reaction mixture was then concentrated under reduced pressure and purified by medium pressure liquid chromatography on silica gel eluting with 0 to 10% methanol in chloroform to provide 0.570 g of the title compound, a compound of the invention, as a solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe crude oil was then redissolved in 10 mL of dichloromethane
  3. stirringstirred for 30 min
  4. stirringstirred at ambient temperature for 16 h
  5. concentrationThe reaction mixture was then concentrated under reduced pressure
  6. custompurified by medium pressure liquid chromatography on silica gel eluting with 0 to 10% methanol in chloroform

Sources & evidence

ORD record
ord-cede0e89192a49b1b1668390e5a9401c
Source dataset
uspto-grants-2015_02
Patent number
US08952024B2

Reaction notes

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