Reaction equation
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.[Cl:7][C:8]1[C:9]2[CH:16]=[CH:15][N:14]([C@H:17]([CH3:20])[CH2:18][OH:19])[C:10]=2[N:11]=[CH:12][N:13]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(Cl)Cl>[Cl:7][C:8]1[C:9]2[CH:16]=[CH:15][N:14]([C@H:17]([CH3:20])[CH2:18][O:19][CH:6]3[CH2:5][CH2:4][CH2:3][CH2:2][O:1]3)[C:10]=2[N:11]=[CH:12][N:13]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
2,3-Dihydropyran (25.0 mL, 270 mmol) was added to (2R)-2-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)propan-1-ol (11.00 g, 51.97 mmol) (see Preparation 3) and pyridinium toluene-4-sulphonate (3.92 g, 15.6 mmol) in DCM (150 mL). The reaction mixture was washed with water (200 mL) and the aqueous phase was extracted with DCM (2×150 mL). The combined organic phases were dried over magnesium sulfate and evaporated in vacuo. The crude material was purified by column chromatography on silica gel (gradient of heptane:EtOAc 100:0 to 70:30) to afford the title compound as a yellow oil in 100% yield, 15.65 g.
Workup
- washThe reaction mixture was washed with water (200 mL)
- extractionthe aqueous phase was extracted with DCM (2×150 mL)
- dry with materialThe combined organic phases were dried over magnesium sulfate
- customevaporated in vacuo
- customThe crude material was purified by column chromatography on silica gel (gradient of heptane:EtOAc 100:0 to 70:30)
Sources & evidence
- ORD record
- ord-b8bda83e3e5d4de991cd9b3d8df6adb2
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08846698B2
Linked notes
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