Ammonia → 7-Chloro-3-(furan-2-yl)-5-(methylsulfanyl)[1,2,4]triazolo[4,3-c]pyrimidine
Reaction equation
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.C[Si](C)(C)O[Si](C)(C)C.[Cl:24][C:25]1[CH:30]=[C:29]([NH:31][NH:32][C:33]([C:35]2[O:36][CH:37]=[CH:38][CH:39]=2)=O)[N:28]=[C:27]([S:40][CH3:41])[N:26]=1.N>C1(C)C(C)=CC=CC=1>[Cl:24][C:25]1[N:26]=[C:27]([S:40][CH3:41])[N:28]2[C:33]([C:35]3[O:36][CH:37]=[CH:38][CH:39]=3)=[N:32][N:31]=[C:29]2[CH:30]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
In an argon atmosphere, 225 g (1.58 mol) of diphosphorus pentaoxide was suspended in 320 mL of xylene, and 340 mL (256 g, 1.58 mol) of hexamethyldisiloxane was added thereto, followed by heating at 90° C. for about 1.5 hours. After the contents were almost dissolved, 90 g (316 mmol) of Compound A was added thereto, followed by heating at 160° C. for another 2 hours. After completion of the reaction, the reaction solution was cooled, and ice-water was added thereto. Then, the mixture was made alkaline by adding aqueous ammonia under cooling (inner temperature: 5° C. or lower), and was extracted with chloroform. After evaporation of the solvent, the residue was purified by silica gel column chromatography (hexane/ethyl acetate=1:1) to obtain 66.1 g of Compound B as a white solid (yield: 78%).
Workup
- dissolutionAfter the contents were almost dissolved
- temperatureby heating at 160° C. for another 2 hours
- customAfter completion of the reaction
- temperaturethe reaction solution was cooled
- temperatureunder cooling (inner temperature: 5° C. or lower)
- extractionwas extracted with chloroform
- customAfter evaporation of the solvent
- customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1:1)
Sources & evidence
- ORD record
- ord-0b4d0d8724cb4d588c81a34079b05d2d
- Source dataset
- uspto-grants-2003_04
- Patent number
- US06545000B1
Reaction notes
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