반응 #7320

반응 방정식

potassium hydroxide

hydroxylamine hydrochloride

uracil

paraformaldehyde

→

5-(hydroxymethyl)-1,3-dihydropyrimidine-2,4-dione

수율 14.5%

용매

water

water

반응 조건

후처리

1. 1
   기타reaction
2. 2
   농축After concentration at 60° C./14 mmHg to a volume of ca. 500 mL
3. 3
   workup.ADDITIONthe residue was diluted with acetone (500 mL)
4. 4
   여과The resulting precipitate was collected by filtration
5. 5
   세척washed with acetone
6. 6
   기타dried by suction
7. 7
   기타at 50° C./25 mmHg to give crude 5-(hydroxymethyl)-1,3-dihydropyrimidine-2,4-dione (250 g) as a white solid
8. 8
   농축The combined mother liquor and washes were concentrated to a volume of ca. 100 mL
9. 9
   여과The resulting precipitate was collected by filtration
10. 10
    세척washed with acetone
11. 11
    기타dried by suction

실험 절차

A 2-L, three-necked flask equipped with a mechanical stirrer, thermometer, condenser, and nitrogen-inlet bubbler was charged with uracil (185.0 g, 1650 mmol) (Aldrich), paraformaldehyde (61.50 g, 2050 mmol as formaldehyde) (Aldrich), and a solution of potassium hydroxide (86.9%, 59.95 g, 928.5 mmol) (Aldrich) in water (1.445 L). The mixture was stirred at 50-52° C. for 68 h. TLC analysis indicated complete reaction. After concentration at 60° C./14 mmHg to a volume of ca. 500 mL, the residue was diluted with acetone (500 mL). The resulting precipitate was collected by filtration, washed with acetone, and dried by suction, then at 50° C./25 mmHg to give crude 5-(hydroxymethyl)-1,3-dihydropyrimidine-2,4-dione (250 g) as a white solid. The combined mother liquor and washes were concentrated to a volume of ca. 100 mL and a solution of hydroxylamine hydrochloride (27.52 g, 396.0 mmol, Aldrich) in water (100 mL) was added. The resulting precipitate was collected by filtration, washed with acetone, and dried by suction to give second crop of crude 5-(hydroxymethyl)-1,3-dihydropyrimidine-2,4-dione (34 g) as a white solid. The two lots were combined (244 g, 4% overweight) and used directly in the next step.

출처