Uracil → HCID 121403973, compound

HRID 2205176Notes

Reaction equation

HRID 2205176 reaction equation
[NH:1]1[CH:8]=[CH:7][C:5](=[O:6])[NH:4][C:2]1=[O:3].C(O[CH:13]1[C@H:17]([O:18][C:19](=[O:21])[CH3:20])[C@H:16]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C@:15]([CH2:33][O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)([CH:30]([F:32])[F:31])[O:14]1)(=O)C.Cl[Sn](Cl)(Cl)Cl>CC#N>[C:19]([O:18][C@@H:17]1[C@H:16]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C@:15]([CH2:33][O:34][CH2:35][C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)([CH:30]([F:31])[F:32])[O:14][C@H:13]1[N:1]1[CH:8]=[CH:7][C:5](=[O:6])[NH:4][C:2]1=[O:3])(=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 1174UracilHCID 24287Tin tetrachlorideHCID 131735802HCID 131735802, compound

Product 1

HCID 121403973HCID 121403973, compoundYield 40.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The mixture of uracil (482 mg, 4.32 mmol) and BSA (1.75 g, 8.64 mmol) in MeCN (20 ml) was stirred at room temperature for 3 hrs. Compound 5 (1.0 g, 2.16 mmol) and SnCl4 (2.4 g, 9.3 mmol) was added respective, then stirred at 65° C. for 12 hrs. The mixture was quenched with saturated NaHCO3 solution, extracted with EtOAc (200 mL×3), dried over Na2SO4 and purified by silica gel chromatography [ethyl acetate:petroleum ether (1:10)] to afford the product (450 mg, 40%) as a yellow solid. LC-MS (M+H)+=517.1

Workup

  1. stirringstirred at 65° C. for 12 hrs
  2. customThe mixture was quenched with saturated NaHCO3 solution
  3. extractionextracted with EtOAc (200 mL×3)
  4. dry with materialdried over Na2SO4
  5. custompurified by silica gel chromatography [ethyl acetate:petroleum ether (1:10)]

Sources & evidence

ORD record
ord-3d5ba0a902b64e46a889d4f37a517cd5
Source dataset
uspto-grants-2016_06
Patent number
US09370569B2

Reaction notes

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