Imidazole → Acetic Acid 5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-diphenyl-silanyloxy)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl Ester

HRID 1645300Notes

Reaction equation

HRID 1645300 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:36]2[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=2)[O:10][CH:11]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:12]2[O:16][CH:15]([N:17]3[CH:22]=[CH:21][C:20](=[O:23])[NH:19][C:18]3=[O:24])[CH:14]([O:25][C:26](=[O:28])[CH3:27])[CH:13]2[OH:29])=[CH:5][CH:4]=1.N1C=CN=C1.[Si:49](Cl)([C:62]([CH3:65])([CH3:64])[CH3:63])([C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1)[C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1.C(OCC)(=O)C>CN(C)C=O>[CH3:43][O:42][C:39]1[CH:38]=[CH:37][C:36]([CH:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[O:10][CH:11]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:12]2[O:16][CH:15]([N:17]3[CH:22]=[CH:21][C:20](=[O:23])[NH:19][C:18]3=[O:24])[CH:14]([O:25][C:26](=[O:28])[CH3:27])[CH:13]2[O:29][Si:49]([C:62]([CH3:65])([CH3:64])[CH3:63])([C:56]2[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=2)[C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)=[CH:41][CH:40]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 8857Ethyl AcetateHCID 94078tert-ButyldiphenylchlorosilaneHCID 131728048Acetic Acid 5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-tetrahydro-furan-3-yl Ester

Product 1

HCID 131728049Acetic Acid 5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-diphenyl-silanyloxy)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl Ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The preparation of tert-butyldiphenylsilyl ethers is a common, routine procedure (Protective Groups in Organic Synthesis, 3rd edition, 1999, pp. 141-144 and references therein, Greene, T. W. and Wuts, P. G. M., eds, Wiley-Interscience, New York). In general, a solution of one eq. of 7 and imidazole (3.5 eq.) in anhydrous N,N-dimethylformamide (DMF) is treated with tert-butyldiphenylsilyl chloride (1.2 eq.). After stirring at room temperature for several hours, the reaction mixture is poured into ethyl acetate and washed extensively with water and saturated brine solution. The resulting organic solution is dried over anhydrous sodium sulfate, filtered, evaporated, and purified by silica gel chromatography to give Compound 8.

Workup

  1. customin Organic Synthesis, 3rd edition, 1999
  2. washwashed extensively with water and saturated brine solution
  3. dry with materialThe resulting organic solution is dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-796a17ac64d040b189e05557c413ddc1
Source dataset
uspto-grants-2012_02
Patent number
US08124745B2

Reaction notes

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