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

HRID 655322

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

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

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

Sources & evidence

ORD record: ord-339f188cbf48461193f25796b8645b08
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08071593B2

Linked notes

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