Hexyl isocyanate → HCID 59310298, compound

HRID 215689Notes

Reaction equation

HRID 215689 reaction equation
[CH2:1]([N:7]=[C:8]=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C[O:11][C:12](=O)[C:13]1[CH:18]=[CH:17][CH:16]=[N:15][C:14]=1[NH2:19]>N1C=CC=CC=1>[CH2:1]([N:7]1[C:12](=[O:11])[C:13]2[CH:18]=[CH:17][CH:16]=[N:15][C:14]=2[NH:19][C:8]1=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 75659Hexyl isocyanateHCID 351633Methyl 2-aminopyridine-3-carboxylate

Product 1

HCID 59310298HCID 59310298, compoundYield 30.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

17.46 g (137.3 mmol, 20 ml)n-hexyl isocyanate was added to a suspension of 5.31 g (34.9 mmol) 2-aminonicotinic acid methyl ester in 130 ml dry pyridine. The mixture was refluxed for 24 hours. The pyridine was removed under reduced pressure and the residue was treated with 160 ml ethanol. The mixture was refluxed for 10 minutes. The crude 3-hexyl-1H-pyrido[2,3-d]pyrimidine-2,4-dione crystallized from the medium and was purified by preparative column chromatography on straight phase silica (eluent:ethyl acetate:cyclohexane 1:2). 3-hexyl-1H-pyrido[2,3-d]pyrimidine-2,4-dione crystallized upon evaporation of the eluent. 2.66 g (310) of 3-hexyl-1H-pyrido[2,3-d]pyrimidine-2,4-dione was isolated (m.p. 166-168° C.)

Workup

  1. temperatureThe mixture was refluxed for 24 hours
  2. customThe pyridine was removed under reduced pressure
  3. additionthe residue was treated with 160 ml ethanol
  4. temperatureThe mixture was refluxed for 10 minutes
  5. customThe crude 3-hexyl-1H-pyrido[2,3-d]pyrimidine-2,4-dione crystallized from the medium
  6. customwas purified by preparative column chromatography on straight phase silica (eluent:ethyl acetate:cyclohexane 1:2)
  7. custom3-hexyl-1H-pyrido[2,3-d]pyrimidine-2,4-dione crystallized upon evaporation of the eluent

Sources & evidence

ORD record
ord-e2df6ccd7e454c438d3443803669cb68
Source dataset
uspto-grants-2012_06
Patent number
US08192918B2

Reaction notes

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