Uracil → 1748-04-5

HRID 1707158Notes

Reaction equation

HRID 1707158 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.Cl[Sn](Cl)(Cl)Cl>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

6

Reactant 4

HCID 1174UracilHCID 13838HexamethyldisilazaneHCID 24287Tin tetrachlorideHCID 81455beta-D-Ribofuranose, 1-acetate 2,3,5-tribenzoate

Product 1

HCID 970461748-04-5Yield 83.1%

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 agitated in 75 ml. of absolute acetonitrile with 0.65 g. (4 mmol) of HMDS, 0.43 g. (4 mmol) of TCS, and 1.56 g. (6 mmol) of SnCl4 for 2 hours at 24° C. The mixture was worked up as set forth in Example 1, yielding 83.1% of crystalline uridine tribenzoate.

Sources & evidence

ORD record
ord-6328c49b2a384b5b84568c56bdc6b36f
Source dataset
uspto-grants-1980_06
Patent number
US04209613

Reaction notes

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