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

HRID 1681870Notes

Reaction equation

HRID 1681870 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 20 h 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. temperatureThe resulting solution was refluxed 20 h
  3. customevaporated to dryness in vacuo
  4. additiondry THF (10 ml) was added
  5. customcrystallization

Sources & evidence

ORD record
ord-2b65149c4fa04a33a00cce150fbb5ab4
Source dataset
uspto-grants-1992_12
Patent number
US05175166

Reaction notes

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