Triethylamine → 6-[Allyl(methyl)amino]-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carbaldehyde

HRID 42701

Reaction equation

HRID 42701 reaction equation
Cl[C:2]1[N:7]([CH3:8])[C:6](=[O:9])[N:5]([CH3:10])[C:4](=[O:11])[C:3]=1[CH:12]=[O:13].C(N(CC)CC)C.[CH3:21][NH:22][CH2:23][CH:24]=[CH2:25]>C(O)C>[CH2:23]([N:22]([CH3:21])[C:2]1[N:7]([CH3:8])[C:6](=[O:9])[N:5]([CH3:10])[C:4](=[O:11])[C:3]=1[CH:12]=[O:13])[CH:24]=[CH2:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 69391N-MethylallylamineHCID 3199716-Chloro-5-formyl-1,3-dimethyluracil

Product 1

HCID 866586896-[Allyl(methyl)amino]-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carbaldehyde

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 6-chloro-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carbaldehyde (0.500 g, 2.47 mmol) and triethyl-amine (0.52 ml, 3.71 mmol) in dry ethanol (10 ml), N-methylprop-2-en-1-amine (0.36 ml, 3.71 mmol) was added under argon. The resulting mixture was stirred at room temperature under argon overnight. After evaporation of the solvent in vacuo, water (15 ml) was added to the yellow oily residue, and the mixture was extracted with dichloromethane (4×15 ml). The combined organic phases were dried over anhydrous MgSO4. The solvent was evaporated in vacuo, and the crude product was purified by crystallization from a mixture of cyclohexane:isopropyl alcohol (4:1).

Workup

  1. customAfter evaporation of the solvent in vacuo, water (15 ml)
  2. additionwas added to the yellow oily residue
  3. extractionthe mixture was extracted with dichloromethane (4×15 ml)
  4. dry with materialThe combined organic phases were dried over anhydrous MgSO4
  5. customThe solvent was evaporated in vacuo
  6. customthe crude product was purified by crystallization from a mixture of cyclohexane:isopropyl alcohol (4:1)

Sources & evidence

ORD record
ord-cc7929173e2d446b981067cd1f9e794d
Source dataset
uspto-grants-2013_09
Patent number
US08536210B2

Linked notes

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