Lithium borohydride → Ether isohexane

HRID 1175387Notes

Reaction equation

HRID 1175387 reaction equation
[CH2:1]([O:3][C:4](=O)[C@H:5]([O:7][C:8]1[CH:13]=[C:12]([NH:14][S:15]([C:18]2[N:19]=[CH:20][N:21]([CH3:23])[CH:22]=2)(=[O:17])=[O:16])[N:11]=[C:10]([S:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[C:27]=2[F:33])[N:9]=1)[CH3:6])[CH3:2].[BH4-].[Li+]>C1COCC1>[CH3:2][CH2:1][O:3][CH2:4][CH3:5].[CH3:29][CH2:28][CH2:27][CH:26]([CH3:31])[CH3:25].[F:33][C:27]1[C:28]([F:32])=[CH:29][CH:30]=[CH:31][C:26]=1[CH2:25][S:24][C:10]1[N:11]=[C:12]([NH:14][S:15]([C:18]2[N:19]=[CH:20][N:21]([CH3:23])[CH:22]=2)(=[O:17])=[O:16])[CH:13]=[C:8]([O:7][C@H:5]([CH3:6])[CH2:4][OH:3])[N:9]=1

Participants

5

Reactant 2

HCID 4148881Lithium borohydrideHCID 536283532-[[2-[[(2,3-difluorophenyl)methyl]thio]-6-[[(1-methyl-1H-imidazol-4-yl)sulfonyl]amino]-4-pyrimidinyl]oxy]-(2R)-propanoic acid ethyl ester

Product 2

HCID 21882825Ether isohexaneHCID 59558752N-[2-[[(2,3-difluorophenyl)methyl]thio]-6-[(1R)-2-hydroxy-1-methylethoxy]-4-pyrimidinyl]-1-methyl-1H-imidazole-4-sulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The title compound was prepared according to the procedure outlined in example 24 using 2-[[2-[[(2,3-difluorophenyl)methyl]thio]-6-[[(1-methyl-1H-imidazol-4-yl)sulfonyl]amino]-4-pyrimidinyl]oxy]-(2R)-propanoic acid ethyl ester (the product of step i) (0.28 g), THF (8 mL) and 2M lithium borohydride in THF (0.81 mL). Purification was by reverse phase HPLC (symmetry as the stationary phase and TFA/acetonitrile as the mobile phase). The resulting oil was triturated with toluene, methanol, then ether/iso-hexane to give the title compound as a white solid. Yield: 0.12 g

Workup

  1. customThe title compound was prepared
  2. customPurification
  3. customThe resulting oil was triturated with toluene, methanol

Sources & evidence

ORD record
ord-40b9611af6c845abae7ac308eb3a65b2
Source dataset
uspto-grants-2010_11
Patent number
US07838675B2

Reaction notes

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