1H-1,2,4-Triazole → 6-Chloro-4-(1H-1,2,4-triazol-1-yl)pyrido[3,2-d]pyrimidin-2-amine

A solution of 1,2,4-triazole (1.4 g, 20 mmol) and phosphorus oxychloride (1.4 mL, 15 mmol) in dry acetonitrile (40 mL) was adder to a stirred suspension of 2-amino-6-chloro-3H-pyrido[3,2-d]pyrimidin-4-one (1 g, 5 mmol) and DIEA (4.4 mL, 25 mmol) in dry acetonitrile (30 mL). The mixture was stirred at room temperature for 24 hours. 2 molar equivalents of 1,2,4-triazole (0.7 g, 10 mmol), 1.5 equivalent of phosphorus oxychloride (0.7 mL, 7.5 mmol) and 2.5 equivalents of DIEA (2.2 mL, 12.5 mmol) were added to the mixture. After stirring at room temperature for 48 hours, the same amount of the above reagents was added again. The reaction mixture was stirred for 7 full days and the yellow precipitate was filtered off, washed successively with acetonitrile, DCM and ether. The solid was dried under vacuum, providing the pure title compound as a yellow solid (667 mg, yield 53%) which was characterised as follows: MS (m/z) 248.8 [M+H]+.

1. stirringAfter stirring at room temperature for 48 hours
2. additionthe same amount of the above reagents was added again
3. stirringThe reaction mixture was stirred for 7 full days
4. filtrationthe yellow precipitate was filtered off
5. washwashed successively with acetonitrile, DCM and ether
6. customThe solid was dried under vacuum

ORD record

ord-72fcdf27270d42258ff759d815c73f73

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08232278B2