Hexamethyldisilazane → 2-Sulfanylidene-1-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-2,3-dihydropyrimidin-4(1H)-one

HRID 1707162Notes

Reaction equation

HRID 1707162 reaction equation
[NH:1]1[CH:8]=[CH:7][C:5](=[O:6])[NH:4][C:2]1=[S: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=[S:3])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 13838HexamethyldisilazaneHCID 24287Tin tetrachlorideHCID 81455beta-D-Ribofuranose, 1-acetate 2,3,5-tribenzoateHCID 1269845Thiouracil

Product 1

HCID 138300342-Sulfanylidene-1-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-2,3-dihydropyrimidin-4(1H)-oneYield 64%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

0.64 g. (5 mmol) of 2-thiouracil, 2.52 g. (5 mmol) of 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose were combined 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 and after 7 hours at 24° C. the mixture was worked up as set forth in Example 1, thus obtaining 64% of crystalline 2-thiouridine tribenzoate.

Sources & evidence

ORD record
ord-e08fad2322454e2985278c4eabc585a2
Source dataset
uspto-grants-1980_06
Patent number
US04209613

Reaction notes

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