Uracil → 1748-04-5

HRID 1707161Notes

Reaction equation

HRID 1707161 reaction equation
[NH:1]1[CH:8]=[CH:7][C:5](=[O:6])[NH:4][C:2]1=[O:3].C(O[C@@H:13]1[O:35][C@H:34]([CH2:36][O:37][C:38](=[O:45])[C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C@@H:24]([O:25][C:26](=[O:33])[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C@H:14]1[O:15][C:16](=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=O)C.C[Si](N[Si](C)(C)C)(C)C>C(#N)C>[C:16]([O:15][C@@H:14]1[C@H:24]([O:25][C:26](=[O:33])[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C@@H:34]([CH2:36][O:37][C:38](=[O:45])[C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[O:35][C@H:13]1[N:1]1[CH:8]=[CH:7][C:5](=[O:6])[NH:4][C:2]1=[O:3])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

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

Product 1

HCID 970461748-04-5Yield 43%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

0.56 g. (5 mmol) of uracil, 2.52 g. (5 mmol) of 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose were refluxed in 70 ml. of absolute acetonitrile with 1.32 g. (12 mmol) of NaBF4, 0.57 g. (3.5 mmol) of HMDS, and 1.68 g. (15.5 mmol) of TCS for 2 hours. The mixture was worked up as set forth in Example 1, yielding 43% of crystalline uridine tribenzoate.

Sources & evidence

ORD record
ord-430ef20498d64a5f9cd44aa506a0428c
Source dataset
uspto-grants-1980_06
Patent number
US04209613

Reaction notes

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