Ethyl orthoformate → Methyl 2-(1H-tetrazol-1-yl)-6,7-dihydro-5H-cyclopenta[d]pyrimidine-6-carboxylate
Reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[CH2:10][CH:9]([C:11]([O:13][CH3:14])=[O:12])[CH2:8][C:6]=2[N:7]=1.FC(F)(F)C(O[Si](C)(C)C)=O.[CH:26](OCC)(OCC)OCC.[N:36]([Si](C)(C)C)=[N+:37]=[N-:38]>C(OCC)(=O)C>[N:1]1([C:2]2[N:3]=[CH:4][C:5]3[CH2:10][CH:9]([C:11]([O:13][CH3:14])=[O:12])[CH2:8][C:6]=3[N:7]=2)[CH:26]=[N:36][N:37]=[N:38]1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a mixture of Methyl 2-amino-6,7-dihydro-5H-cyclopenta[d]pyrimidine-6-carboxylate (65.2 mg, 0.364 mmol) in ethyl acetate (5 mL) was added trimethylsilyl trifluoroacetate (0.107 mL, 0.619 mmol) at room temperature. The mixture was stirred at room temperature then triethyl orthoformate (0.103 mL, 0.619 mmol) was added. The mixture was stirred for another 5 minutes then azidotrimethylsilane (0.081 mL, 0.619 mmol) was added. The reaction was stirred at room temperature overnight then concentrated in vacuo and the residue was triturated twice with dichloromethane. The resulting solid was collected by centrifugation and dried in vacuo to afford the title compound: LC/MS: [(M+1)]+=233.
Workup
- stirringThe mixture was stirred for another 5 minutes
- stirringThe reaction was stirred at room temperature overnight
- concentrationthen concentrated in vacuo
- customthe residue was triturated twice with dichloromethane
- customThe resulting solid was collected by centrifugation
- customdried in vacuo
Sources & evidence
- ORD record
- ord-f851af3a751140f1915c567b8ce03c50
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09062070B2
Reaction notes
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