Pyridine → HCID 11820436, compound

HRID 269794Notes

Reaction equation

HRID 269794 reaction equation
[CH2:1]([NH:4][C:5]([NH:7][CH2:8][CH2:9][CH3:10])=[O:6])[CH2:2][CH3:3].C(O[C:15](=[O:17])[CH3:16])(=O)C.N1C=CC=[CH:20][CH:19]=1>CN(C)C1C=CN=CC=1>[CH3:19][C:20]1[N:7]([CH2:8][CH2:9][CH3:10])[C:5](=[O:6])[N:4]([CH2:1][CH2:2][CH3:3])[C:15](=[O:17])[CH:16]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 69343N,N'-Dipropylurea

Product 1

HCID 11820436HCID 11820436, compound

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Conditions

Temperature
95 °C

Procedure

To a solution of N,N′ Dipropyl urea (10.0 g, 69.4 mmol) in pyridine (60 ml) was added acetic anhydride (21.6 ml, 229 mmol) and 4-(dimethylamino)pyridine (8.5 g, 69.4 mmol). The mixture was heated to 95° C. for 1.5 hours. The reaction mixture was cooled and the solvent was removed under vacuum. The residue was then dissolved in dichloromethane (200 ml) and washed with 2N HCl (2×60 ml) and saturated sodium bicarbonate (2×60 ml). The organic layer was concetrated and purified using column chromatography (2:1 Hexane:Ethyl Acetate) to yield 6-methyl-1,3-dipropyl-1,3-dihydropyrimidine-2,4-dione(4.0 g, M+1=210.92)

Workup

  1. temperatureThe reaction mixture was cooled
  2. customthe solvent was removed under vacuum
  3. dissolutionThe residue was then dissolved in dichloromethane (200 ml)
  4. washwashed with 2N HCl (2×60 ml) and saturated sodium bicarbonate (2×60 ml)
  5. custompurified

Sources & evidence

ORD record
ord-a1788df02570463399f70c1bf0b66bce
Source dataset
uspto-grants-2008_11
Patent number
US07449473B2

Reaction notes

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