Lithium borohydride → Ether isohexane

HRID 1024975Notes

Reaction equation

HRID 1024975 reaction equation
[F:1][C:2]1[C:34]([F:35])=[CH:33][CH:32]=[CH:31][C:3]=1[CH2:4][S:5][C:6]1[N:11]=[C:10]([O:12][C@H:13]([CH3:19])[C:14](OCC)=[O:15])[CH:9]=[C:8]([NH:20][S:21]([C:24]2[N:25]=[C:26]([CH3:30])[N:27]([CH3:29])[CH:28]=2)(=[O:23])=[O:22])[N:7]=1.[BH4-].[Li+]>C1COCC1>[CH3:9][CH2:10][O:12][CH2:13][CH3:14].[CH3:33][CH2:34][CH2:2][CH:3]([CH3:31])[CH3:4].[F:1][C:2]1[C:34]([F:35])=[CH:33][CH:32]=[CH:31][C:3]=1[CH2:4][S:5][C:6]1[N:7]=[C:8]([NH:20][S:21]([C:24]2[N:25]=[C:26]([CH3:30])[N:27]([CH3:29])[CH:28]=2)(=[O:23])=[O:22])[CH:9]=[C:10]([O:12][C@H:13]([CH3:19])[CH2:14][OH:15])[N:11]=1

Participants

5

Reactant 2

HCID 4148881Lithium borohydrideHCID 53628392HCID 53628392, compound

Product 2

HCID 21882825Ether isohexaneHCID 59558844N-{2-[(2,3-Difluorobenzyl)thio]-6-[(1R)-2-hydroxy-1-methylethoxy]pyrimidin-4-yl}-1,2-dimethyl-1H-imidazole-4-sulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared according to the procedure outlined in example 11 using a mixture of ethyl (2R)-2-[(2-[(2,3-difluorobenzyl)thio]-6-{[(1,2-dimethyl-1H-imidazol-4-yl)sulfonyl]amino}pyrimidin-4-yl)oxy]propanoate (the product from step (i) (0.25 g), lithium borohydride (2M solution in THF, 0.48 mL) and THF (6 mL). Purification was by reverse phase HPLC (symmetry as the stationary phase and TFA/acetonitrile as the mobile phase) then titurated with Toluene, DCM and then Et2O/iso-hexane to give the title compound as a white solid, 44 mg

Workup

  1. customThe title compound was prepared
  2. customPurification

Sources & evidence

ORD record
ord-8e74db7cff8d45a6ab0499e086438030
Source dataset
uspto-grants-2014_05
Patent number
US08722883B2

Reaction notes

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