Lithium borohydride → Ether isohexane

HRID 2388848Notes

Reaction equation

HRID 2388848 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 (2 M 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. Yield: 44 mg

Workup

  1. customThe title compound was prepared
  2. customPurification

Sources & evidence

ORD record
ord-67ef038e24f94121bca84d9ee6471f60
Source dataset
uspto-grants-2012_09
Patent number
US08269002B2

Reaction notes

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