Dimethylformamide → HCID 86607310, compound

HRID 552709Notes

Reaction equation

[Cl: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][CH2:22][S:23]([O-:26])(=O)=[O:24])[O:12]1.C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)[Cl:45].CN(C)C=O.S(Cl)(Cl)=O>>[Cl: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][CH2:22][S:23]([Cl:45])(=[O:26])=[O:24])[O:12]1

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 6344Dichloromethane

HCID 24386Thionyl Chloride

HCID 86607311HCID 86607311, compound

Product 1

HCID 86607310HCID 86607310, compoundYield 78.1%

Conditions

Temperature: 0 °C

Procedure

Tetrabutyl-ammonium 2-[(3aR,4R,6R,6aR)-6-(6-chloro-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-ethanesulfonate (250.0 mg, 0.0003481 mol) was dissolved in methylene chloride (5.00 mL, 0.0780 mol) and N,N-dimethylformamide (100.0 μL, 0.001292 mol). Thionyl chloride (228 μL, 0.00313 mol) was added and the reaction was stirred at 0° C. for 45 minutes, concentrated in vacuo to dryness and followed by azeotroping with toluene. The residue was purified by flash chromatography (10% THF in DCM) to yield product (115 mg, 78%).

Workup

concentrationconcentrated in vacuo to dryness
customby azeotroping with toluene
customThe residue was purified by flash chromatography (10% THF in DCM)

Sources & evidence

ORD record: ord-a921e1cf460f4829a963f5de60c184bf
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07951810B2

Reaction notes

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