3-Ethoxy-2-methylacrylaldehyde → Methyl 3-(5-methylpyrimidin-2-yl)benzoate

HRID 1970868Notes

Reaction equation

HRID 1970868 reaction equation
C(O)(=O)C.[C:5]([C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=1)[C:11]([O:13][CH3:14])=[O:12])(=[NH:7])[NH2:6].CCO/[CH:21]=[C:22](/[CH:24]=O)\[CH3:23].C[O-].[Na+]>CO>[CH3:24][C:22]1[CH:21]=[N:7][C:5]([C:8]2[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=2)[C:11]([O:13][CH3:14])=[O:12])=[N:6][CH:23]=1

Participants

5

Reactant 3

HCID 30848683-Ethoxy-2-methylacrylaldehydeHCID 10942334Sodium MethoxideHCID 66985510HCID 66985510, compound

Product 1

HCID 59484867Methyl 3-(5-methylpyrimidin-2-yl)benzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
50 °C

Procedure

2.41 g (10 mmol) of methyl 3-carbamimidoylbenzoate acetate are suspended in 40 ml of methanol, 1.31 ml (11 mmol) of 3-ethoxymethacrolein and 2.04 ml of 30% sodium methoxide in methanol are added, and the mixture is stirred at 50° C. for 15 h. The reaction mixture is evaporated to dryness, and 100 ml of water are added. The precipitate formed is filtered off with suction and dried in vacuo. The crude product is reacted further without further purification; product: 1.65 g; ESI: 229 (M+H).

Workup

  1. customThe reaction mixture is evaporated to dryness, and 100 ml of water
  2. additionare added
  3. customThe precipitate formed
  4. filtrationis filtered off with suction
  5. customdried in vacuo
  6. customThe crude product is reacted further without further purification

Sources & evidence

ORD record
ord-917329a1ffb74308bb3d65f5d0898077
Source dataset
uspto-grants-2013_04
Patent number
US08431572B2

Reaction notes

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