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

HRID 1598

Reaction equation

HRID 1598 reaction equation
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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-47a44d0423b048a0ba771f9e6b7956a7
Source dataset
uspto-grants-1998_03
Patent number
US05726179

Linked notes

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