反応 #7320

反応方程式

potassium hydroxide

hydroxylamine hydrochloride

uracil

paraformaldehyde

→

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

収率 14.5%

溶媒

water

water

反応条件

後処理

1. 1
   その他reaction
2. 2
   濃縮After 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
   ろ過The resulting precipitate was collected by filtration
5. 5
   洗浄washed with acetone
6. 6
   その他dried by suction
7. 7
   その他at 50° C./25 mmHg to give crude 5-(hydroxymethyl)-1,3-dihydropyrimidine-2,4-dione (250 g) as a white solid
8. 8
   濃縮The combined mother liquor and washes were concentrated to a volume of ca. 100 mL
9. 9
   ろ過The resulting precipitate was collected by filtration
10. 10
    洗浄washed with acetone
11. 11
    その他dried by suction

実験手順

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.

出典