Ammonia → HCID 67164793, compound

HRID 552751Notes

Reaction equation

HRID 552751 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@H:11]1[C@@H:15]2[O:16][C:17]([CH3:20])([CH3:19])[O:18][C@@H:14]2[C@@H:13]([CH2:21][OH:22])[O:12]1.C[Si](Cl)(C)C.[Br:28][C:29]1[CH:37]=[CH:36][C:32]([C:33](Cl)=[O:34])=[CH:31][CH:30]=1.N>N1C=CC=CC=1.O>[Br:28][C:29]1[CH:37]=[CH:36][C:32]([C:33]([NH:1][C:2]2[N:10]=[CH:9][N:8]=[C:7]3[C:3]=2[N:4]=[CH:5][N:6]3[C@H:11]2[C@H:15]3[C@H:14]([O:18][C:17]([CH3:19])([CH3:20])[O:16]3)[C@@H:13]([CH2:21][OH:22])[O:12]2)=[O:34])=[CH:31][CH:30]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 6397ChlorotrimethylsilaneHCID 685154-Bromobenzoyl chlorideHCID 2723654362-75-4

Product 1

HCID 67164793HCID 67164793, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent2×

Conditions

Temperature
0 °C

Procedure

[(3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]methanol (0.400 g, 1.30 mmol) was dried by co-evaporation with pyridine, then suspended in dry pyridine (6.5 mL). TMSCl (0.330 mL, 2.60 mmol) was added and the mixture was stirred for 15 min. 4-Bromobenzoylchloride (0.342 g, 1.56 mmol) was added to the mixture and stirred for 2 h. The solution was cooled to 0° C. and 1 mL of H2O was added. After 5 min a 29% NH3 aq solution (0.847 mL) was added and the reaction mixture was stirred for 30 min while warming to r.t. The mixture was then concentrated and the residue was diluted with H2O (40 mL). The product was extracted with EtOAc (60 mL) and concentrated. The crude material was purified by flash chromatography (65 to 100% EtOAc/hexanes) to afford the title compound (0.305 g, 49%).

Workup

  1. stirringstirred for 2 h
  2. stirringthe reaction mixture was stirred for 30 min
  3. temperaturewhile warming to r.t
  4. concentrationThe mixture was then concentrated
  5. additionthe residue was diluted with H2O (40 mL)
  6. extractionThe product was extracted with EtOAc (60 mL)
  7. concentrationconcentrated
  8. customThe crude material was purified by flash chromatography (65 to 100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-bb4517ba29a748ebb3d3a55c4b8145aa
Source dataset
uspto-grants-2011_05
Patent number
US07951810B2

Reaction notes

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