Lithium borohydride → N-[2-[[(2,3-difluorophenyl)methyl]thio]-6-[(1R)-2-hydroxy-1-methylethoxy]-4-pyrimidinyl]-methanesulfonamide

HRID 1958930Notes

Reaction equation

HRID 1958930 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]([CH3:18])(=[O:17])=[O:16])[N:11]=[C:10]([S:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[C:22]=2[F:28])[N:9]=1)[CH3:6])[CH3:2].[BH4-].[Li+]>C1COCC1>[CH3:2][CH2:1][O:3][CH2:4][CH3:5].[CH3:24][CH2:23][CH2:22][CH:21]([CH3:26])[CH3:20].[F:28][C:22]1[C:23]([F:27])=[CH:24][CH:25]=[CH:26][C:21]=1[CH2:20][S:19][C:10]1[N:11]=[C:12]([NH:14][S:15]([CH3:18])(=[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 670512712-[[2-[[(2,3-difluorophenyl)methyl]thio]-6-[(methylsulfonyl)amino)-4-pyrimidinyl]oxy]-(2R)-propanoic acid ethyl ester

Product 2

HCID 11632815N-[2-[[(2,3-difluorophenyl)methyl]thio]-6-[(1R)-2-hydroxy-1-methylethoxy]-4-pyrimidinyl]-methanesulfonamideHCID 21882825Ether isohexane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The title compound was prepared according to the procedure outlined in example 24 using a mixture of 2-[[2-[[(2,3-difluorophenyl)methyl]thio]-6-[(methylsulfonyl)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 (1.3 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, DCM, then ether/iso-hexane to give the title compound as a white solid. Yield: 0.18 g

Workup

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

Sources & evidence

ORD record
ord-0f1690ce24274293830b488667763af6
Source dataset
uspto-grants-2013_04
Patent number
US08410123B2

Reaction notes

Loading…