Ethanol → 1,4,5,6-Tetrahydro-5-ethoxycarbonylpyrimidine Hydrochloride

HRID 1653703

Reaction equation

HRID 1653703 reaction equation
Cl.[NH:2]1[CH2:7][CH:6]([C:8]([OH:10])=[O:9])[CH2:5][N:4]=[CH:3]1.S(Cl)([Cl:13])=O.[CH2:15](O)[CH3:16]>>[ClH:13].[CH2:15]([O:9][C:8]([CH:6]1[CH2:7][NH:2][CH:3]=[N:4][CH2:5]1)=[O:10])[CH3:16]

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 703421841,4,5,6-Tetrahydropyrimidine-5-carboxylic acid hydrochloride

Product 1

HCID 200804501,4,5,6-Tetrahydro-5-ethoxycarbonylpyrimidine HydrochlorideYield 63%

Procedure

1,4,5,6-Tetrahydropyrimidine-5-carboxylic acid hydrochloride (1.5 g, 9.12 mmol) was dissolved in absolute ethanol (40 ml) by heating. The thionyl chloride (1.1 g, 9.16 mmol) was added dropwise with stirring. The resulting solution was refluxed 20h and then evaporated to dryness in vacuo. The residue was taken up in absolute methanol (5 ml) and dry THF (10 ml) was added to induce crystallization, giving 1.1 g (63%) product as white crystals, mp 125°-127° C. 300 MHz nmr confirmed the product. Microanalysis calc.: C 43.64, H 6.75, N 14.55; found: C, 43.43, H 6.58, N 14.40.

Workup

  1. temperatureby heating
  2. customevaporated to dryness in vacuo
  3. additiondry THF (10 ml) was added
  4. customcrystallization

Sources & evidence

ORD record
ord-0a47118198fe430299b368f7293bee1b
Source dataset
uspto-grants-1995_04
Patent number
US05403845

Linked notes

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