Реакция #1694

Уравнение реакции

1,4,5,6-tetrahydropyrimidine-5-carboxylic acid hydrochloride

oxalyl chloride

2-butyn-l-ol

→

5-(2-butynyloxycarbonyl)-1,4,5,6-tetrahydropyrimidine

Выход 61.0%

Растворители

water

benzene

Условия реакции

Обработка

1. 1
   Температураheated
2. 2
   Температураunder reflux for 2.5 h
3. 3
   Другоеevaporated to dryness in vacuo
4. 4
   Температураafter cooling
5. 5
   Другоеto give an orange-yellow residue
6. 6
   workup.STIRRINGwas stirred at room temperature overnight
7. 7
   workup.STIRRINGAfter stirring overnight
8. 8
   Другоеthe solvents were removed in vacuo
9. 9
   Другоеto give a brownish residue
10. 10
    workup.STIRRINGstirred at room temperature for 2 h
11. 11
    Фильтрацияfiltered
12. 12
    ДругоеThe brown residue obtained on removal of the solvents in vacuo
13. 13
    Другоеwas recrystallized (ethanol/ether)

Методика

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.

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