Methanol → 5-(thiophen-2-yl)pyrimidine-2,4(1H,3H)-dione
Reaction equation
C([O:8][C:9]1[N:14]=[C:13]([O:15]CC2C=CC=CC=2)[C:12]([C:23]2[S:24][CH:25]=[CH:26][CH:27]=2)=[CH:11][N:10]=1)C1C=CC=CC=1.I[Si](C)(C)C.CO>ClCCl>[S:24]1[CH:25]=[CH:26][CH:27]=[C:23]1[C:12]1[C:13](=[O:15])[NH:14][C:9](=[O:8])[NH:10][CH:11]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 2,4-bis(benzyloxy)-5-(thiophen-2-yl)pyrimidine (Prep21, 20 g, 53.5 mol) in dry dichloromethane (400 ml), iodotrimethylsilane (28.8 g, 0.14 mol) was added at room temperature. The resulting solution was stirred for 3 hours. Then methanol was added, the precipitate was filtered and the solid was recrystallized with methanol twice, to afford 7 g of the title compound (y=67.3%)
Workup
- filtrationthe precipitate was filtered
- customthe solid was recrystallized with methanol twice
Sources & evidence
- ORD record
- ord-55783d39b8ab4b05beb31932ffdd20fc
- Source dataset
- uspto-grants-2011_10
- Patent number
- US08030322B2
Reaction notes
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