2,2,2-trifluoro-N-(prop-2-yn-1-yl)acetamide → Acetamide, 2,2,2-trifluoro-N-propyl-
Reaction equation
[F:1][C:2]([F:10])([F:9])[C:3]([NH:5][CH2:6][C:7]#[CH:8])=[O:4].[H][H]>[Pd]>[F:1][C:2]([F:10])([F:9])[C:3]([NH:5][CH2:6][CH2:7][CH3:8])=[O:4]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
In Reaction Scheme 4,6-amino-4-methoxypyrazolo[3,4-d]pyrimidine was converted to the iodo derivative (14) which was treated with 1-chloro-1,2-dideoxy-3,5-di-O-toluoylribofuranose to yield the nucleoside (15). Compound (15) was treated with NaOMe/MeOH to hydrolyze the toluoyl groups and yield the unblocked nucleoside (16). Treatment of (16) with aqueous sodium hydroxide gave (17) which could be converted to the trifluoro-N-prop-2-ynyl acetamide derivative (18). Compound (18) was reduced with hydrogen and a Pd catalyst to yield the trifluoro-N-propylacetamide derivative (19). The 4-amino group of compound (19) was protected by treatment with N,N-dimethylformamide dimethylacetal to give compound (20) which was converted to DMTr derivative (21) and then to the phosphoramidite derivative (22).
Sources & evidence
- ORD record
- ord-7b42368841d24de78aba4da52ae85f99
- Source dataset
- uspto-grants-2010_07
- Patent number
- US07751982B2
Reaction notes
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