Uracil → 1748-04-5

HRID 1707160Notes

Reaction equation

HRID 1707160 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 40%

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 1.41 g. (12 mmol) of NH4ClO4, 0.57 g. (3.5 mmol) of HMDS, and 1.68 g. (15.5 mmol) of TCS for 20 hours. The mixture was worked up as set forth in Example 1, thus producing 40% of crystalline uridine tribenzoate.

Sources & evidence

ORD record
ord-04696b56b2f94a1ebe91ae54aa5d550a
Source dataset
uspto-grants-1980_06
Patent number
US04209613

Reaction notes

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