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

HRID 1024880Notes

Reaction equation

HRID 1024880 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]([CH:18]2[CH2:20][CH2:19]2)(=[O:17])=[O:16])[N:11]=[C:10]([S:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[C:24]=2[F:30])[N:9]=1)[CH3:6])[CH3:2].[BH4-].[Li+]>C1COCC1>[CH3:2][CH2:1][O:3][CH2:4][CH3:5].[CH3:26][CH2:25][CH2:24][CH:23]([CH3:28])[CH3:22].[F:30][C:24]1[C:25]([F:29])=[CH:26][CH:27]=[CH:28][C:23]=1[CH2:22][S:21][C:10]1[N:11]=[C:12]([NH:14][S:15]([CH:18]2[CH2:19][CH2:20]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 670512192-[[6-[(cyclopropylsulfonyl)amino]-2-[[(2,3-difluorophenyl)methyl]thio]-4-pyrimidinyl]oxy]-(2R)-propanoic acid ethyl ester

Product 2

HCID 11546492N-[2-[[(2,3-difluorophenyl)methyl]thio]-6-[(1R)-2-hydroxy-1-methylethoxy]-4-pyrimidinyl]-cyclopropanesulfonamideHCID 21882825Ether isohexane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The title compound was prepared according to the procedure outlined in example 24 using 2-[[6-[(cyclopropylsulfonyl)amino]-2-[[(2,3-difluorophenyl)methyl]thio]-4-pyrimidinyl]oxy]-(2R)-propanoic acid ethyl ester, (the product of step i) (0.30 g), THF (8 mL) and 2M lithium borohydride in THF (2 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 methanol, toluene, DCM, then ether/iso-hexane to give the title compound as a white solid. Yield: 0.20 g

Workup

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

Sources & evidence

ORD record
ord-2581380c2d4b47f4b27256daf22d53ec
Source dataset
uspto-grants-2014_05
Patent number
US08722883B2

Reaction notes

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