Uracil → 1748-04-5

HRID 1707159Notes

Reaction equation

HRID 1707159 reaction equation
[NH:1]1[CH:8]=[CH:7][C:5](=[O:6])[NH:4][C:2]1=[O:3].C[Si](N[Si](C)(C)C)(C)C.C(O[C@@H:22]1[O:44][C@H:43]([CH2:45][O:46][C:47](=[O:54])[C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[C@@H:33]([O:34][C:35](=[O:42])[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C@H:23]1[O:24][C:25](=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)(=O)C>C(#N)C>[C:25]([O:24][C@@H:23]1[C@H:33]([O:34][C:35](=[O:42])[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C@@H:43]([CH2:45][O:46][C:47](=[O:54])[C:48]2[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=2)[O:44][C@H:22]1[N:1]1[CH:8]=[CH:7][C:5](=[O:6])[NH:4][C:2]1=[O:3])(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 1174UracilHCID 13838HexamethyldisilazaneHCID 81455beta-D-Ribofuranose, 1-acetate 2,3,5-tribenzoate

Product 1

HCID 970461748-04-5Yield 58%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

0.56 g. (5 mmol) of uracil was agitated in 70 ml. of absolute acetonitrile with 1.86 g. (3.5 mmol) of HMDS and 2.55 g. (15.5 mmol) of TCS, as well as 1.69 g. (12 mmol) of NaClO4.H2O for 30 minutes at 24° C. The reaction mixture was then combined with 2.52 g. (5 mmol) of 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose and refluxed for 20 hours. The mixture was worked up as described in Example 1, yielding 58% of crystalline uridine tribenzoate.

Sources & evidence

ORD record
ord-1ddd0188b0694365af3ce008374c9efc
Source dataset
uspto-grants-1980_06
Patent number
US04209613

Reaction notes

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