Water → 8-amino-7-chloro-2H-[1,2,4]triazolo[4,3-c]pyrimidin-3-one

To a solution of 5-amino-4,6-dichloropyrimidine (1.64 g, 10 mmol) in THF (10 mL) at room temperature under argon was added H2NNH2 (0.96 g mg, 30 mmol). The resulting reaction mixture was stirred at room temperature under argon for 50 h. HPLC analysis indicated disappearance of the starting material. Water (100 mL) was added to the reaction mixture. The solid precipitate was collected by filtration and was washed with water (10 mL×3). The resulting solid was dissolved in a mixture of 20 mL of 1 M aqueous HCl and 10 mL of 1,4-dioxane. Triphosgene (7.6 g, 25.7 mmol) was then added. After the reaction mixture had stirred at room temperature under argon for 3 h, analysis by HPLC/MS indicated that the reaction was complete. Water (50 mL) was added to the reaction mixture. The solid precipitate was collected by filtration and was washed with water (5 mL×3). After the resulting solid was dried under vacuum, the title compound (1.41 g) was obtained as a tan solid. HPLC/MS: retention time=0.93 min, [M+H]30 =186. See also C. Temple, Jr., et al., J. Org. Chem., volume 33, pp. 530-533, 1968.

1. customThe resulting reaction mixture
2. filtrationThe solid precipitate was collected by filtration
3. washwas washed with water (10 mL×3)
4. dissolutionThe resulting solid was dissolved in a mixture of 20 mL of 1 M aqueous HCl and 10 mL of 1,4-dioxane
5. stirringAfter the reaction mixture had stirred at room temperature under argon for 3 h
6. filtrationThe solid precipitate was collected by filtration
7. washwas washed with water (5 mL×3)
8. customAfter the resulting solid was dried under vacuum

ORD record

ord-c8c37e58b8c0444bb52c8f21c1388fb7

Source dataset

uspto-grants-2008_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07452892B2