2-Butyn-1-ol → 5-(2-Butynyloxycarbonyl)-1,4,5,6-tetrahydropyrimidine

HRID 1598

Reaktionsgleichung

Reaktionsgleichung von HRID 1598
Cl.[NH:2]1[CH2:7][CH:6]([C:8]([OH:10])=[O:9])[CH2:5][N:4]=[CH:3]1.C(Cl)(=O)C(Cl)=O.[CH2:17](O)[C:18]#[C:19][CH3:20]>C1C=CC=CC=1.O>[CH2:17]([O:9][C:8]([CH:6]1[CH2:7][NH:2][CH:3]=[N:4][CH2:5]1)=[O:10])[C:18]#[C:19][CH3:20]

Komponenten

6

Edukt 3

HCID 129912-Butyn-1-olHCID 65578Oxalyl chlorideHCID 703421841,4,5,6-Tetrahydropyrimidine-5-carboxylic acid hydrochloride

Produkt 1

HCID 106074585-(2-Butynyloxycarbonyl)-1,4,5,6-tetrahydropyrimidineAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

1,4,5,6-tetrahydropyrimidine-5-carboxylic acid hydrochloride (1 g, 6 mmol) was suspended in a solution of oxalyl chloride (1.5 mL, 17 mmol) in benzene (10 mL), heated with stirring under reflux for 2.5 h, and then evaporated to dryness in vacuo after cooling, to give an orange-yellow residue. A mixture of the acid chloride (04 g) and 2-butyn-l-ol (20 mL, excess) was stirred at room temperature overnight. After stirring overnight, the solvents were removed in vacuo to give a brownish residue. The residue was taken up in water (100 mL), stirred at room temperature for 2 h and filtered. The brown residue obtained on removal of the solvents in vacuo was recrystallized (ethanol/ether) to give a brown viscous oil (0.3 g, 61%) of 5-(2-butynyloxycarbonyl)-1,4,5,6-tetrahydropyrimidine as the hydrochloride salt. 1H NMR (D2O): δ 1.5 (t, 3H, CH3), 3.1 (m, 1H), 3.5 (d, 4H), 3.9 (q, 2H, OCH2), 7.9 (s, 1H, amidine-H). Anal. (C9H13N2O2Cl) C, H, N.

Aufarbeitung

  1. temperatureheated
  2. temperatureunder reflux for 2.5 h
  3. customevaporated to dryness in vacuo
  4. temperatureafter cooling
  5. customto give an orange-yellow residue
  6. stirringwas stirred at room temperature overnight
  7. stirringAfter stirring overnight
  8. customthe solvents were removed in vacuo
  9. customto give a brownish residue
  10. stirringstirred at room temperature for 2 h
  11. filtrationfiltered
  12. customThe brown residue obtained on removal of the solvents in vacuo
  13. customwas recrystallized (ethanol/ether)

Quellen und Nachweise

ORD-Eintrag
ord-47a44d0423b048a0ba771f9e6b7956a7
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05726179

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