Methanol → 5-(thiophen-2-yl)pyrimidine-2,4(1H,3H)-dione

HRID 1661058Notes

Reaction equation

HRID 1661058 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]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 85247Trimethylsilyl iodideHCID 12118032,4-Bis(benzyloxy)-5-(thiophen-2-yl)pyrimidine

Product 1

HCID 8190965-(thiophen-2-yl)pyrimidine-2,4(1H,3H)-dioneYield 67.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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

  1. filtrationthe precipitate was filtered
  2. 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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